Photoinduced Dynamic Radical Processes for Isomerizations, Deracemizations, and Dynamic Kinetic Resolutions

DeHovitz, Jacob S.; Hyster, Todd K.

doi:10.1021/acscatal.2c02480

Photoinduced Dynamic Radical Processes for Isomerizations, Deracemizations, and Dynamic Kinetic Resolutions

Journal Article · 11 July 2022 · ACS Catalysis

DOI:https://doi.org/10.1021/acscatal.2c02480· OSTI ID:1978323

DeHovitz, Jacob S. ^[1]; ^[2]

Department of Chemistry, University of California, Berkeley, California 94720, United States
Department of Chemistry and Chemical Biology, Cornell University, Ithaca, New York 14853, United States

Not provided.

Research Organization:: Princeton Univ., NJ (United States)

Sponsoring Organization:: USDOE Office of Science (SC)

DOE Contract Number:: SC0019370

OSTI ID:: 1978323

Journal Information:: ACS Catalysis, Vol. 12, Issue 15; ISSN 2155-5435

Publisher:: American Chemical Society (ACS)

Country of Publication:: United States

Language:: English

References (114)

Asymmetric Catalysis Special Feature Part I: Asymmetric catalysis in complex target synthesis Taylor, M. S.; Jacobsen, E. N. Proceedings of the National Academy of Sciences, Vol. 101, Issue 15 https://doi.org/10.1073/pnas.0307893101	journal	March 2004
Double Asymmetric Synthesis and a New Strategy for Stereochemical Control in Organic Synthesis Masamune, Satoru; Choy, William; Petersen, John S. Angewandte Chemie International Edition in English, Vol. 24, Issue 1 https://doi.org/10.1002/anie.198500013	journal	January 1985
Substrate-directable chemical reactions Hoveyda, Amir H.; Evans, David A.; Fu, Gregory C. Chemical Reviews, Vol. 93, Issue 4 https://doi.org/10.1021/cr00020a002	journal	June 1993
Recent Progress and Developments in Chemoenzymatic and Biocatalytic Dynamic Kinetic Resolution Yang, Li-Cheng; Deng, Heping; Renata, Hans Organic Process Research & Development, Vol. 26, Issue 7 https://doi.org/10.1021/acs.oprd.1c00463	journal	February 2022
Organocatalytic Dynamic Kinetic Resolution: An Update Pellissier, Hélène European Journal of Organic Chemistry, Vol. 2022, Issue 7 https://doi.org/10.1002/ejoc.202101561	journal	February 2022
Racemisation in Chemistry and Biology Ballard, Andrew; Narduolo, Stefania; Ahmed, Hiwa O. Chemistry – A European Journal, Vol. 26, Issue 17 https://doi.org/10.1002/chem.201903917	journal	March 2020
Development of a Concise, Asymmetric Synthesis of a Smoothened Receptor (SMO) Inhibitor: Enzymatic Transamination of a 4-Piperidinone with Dynamic Kinetic Resolution Peng, Zhihui; Wong, John W.; Hansen, Eric C. Organic Letters, Vol. 16, Issue 3 https://doi.org/10.1021/ol403630g	journal	January 2014
Dynamic Kinetic Resolution of Phthalides via Asymmetric Transfer Hydrogenation: A Strategy Constructs 1,3-Distereocentered 3-(2-Hydroxy-2-arylethyl)isobenzofuran-1(3H)-one Cheng, Tanyu; Ye, Qunqun; Zhao, Qiankun Organic Letters, Vol. 17, Issue 20 https://doi.org/10.1021/acs.orglett.5b02394	journal	October 2015
Efficient catalytic racemization of secondary alcohols Koh, Jeong Hwan; Jeong, Hyun Min; Park, Jaiwook Tetrahedron Letters, Vol. 39, Issue 31 https://doi.org/10.1016/S0040-4039(98)01116-2	journal	July 1998
Lipase-Catalyzed Dynamic Kinetic Resolution of Chiral Amines: Use of Palladium as the Racemization Catalyst Reetz, Manfred T.; Schimossek, Klaus CHIMIA, Vol. 50, Issue 12 https://doi.org/10.2533/chimia.1996.668	journal	December 1996
Radicals: Reactive Intermediates with Translational Potential Yan, Ming; Lo, Julian C.; Edwards, Jacob T. Journal of the American Chemical Society, Vol. 138, Issue 39 https://doi.org/10.1021/jacs.6b08856	journal	September 2016
Metallaphotoredox: The Merger of Photoredox and Transition Metal Catalysis Chan, Amy Y.; Perry, Ian B.; Bissonnette, Noah B. Chemical Reviews, Vol. 122, Issue 2 https://doi.org/10.1021/acs.chemrev.1c00383	journal	November 2021
Photoredox Catalysis in Organic Chemistry Shaw, Megan H.; Twilton, Jack; MacMillan, David W. C. The Journal of Organic Chemistry, Vol. 81, Issue 16 https://doi.org/10.1021/acs.joc.6b01449	journal	June 2016
Visible Light Photoredox Catalysis with Transition Metal Complexes: Applications in Organic Synthesis Prier, Christopher K.; Rankic, Danica A.; MacMillan, David W. C. Chemical Reviews, Vol. 113, Issue 7 https://doi.org/10.1021/cr300503r	journal	March 2013
Organic Photoredox Catalysis Romero, Nathan A.; Nicewicz, David A. Chemical Reviews, Vol. 116, Issue 17 https://doi.org/10.1021/acs.chemrev.6b00057	journal	June 2016
Synthetic Organic Electrochemical Methods Since 2000: On the Verge of a Renaissance Yan, Ming; Kawamata, Yu; Baran, Phil S. Chemical Reviews, Vol. 117, Issue 21 https://doi.org/10.1021/acs.chemrev.7b00397	journal	October 2017
Advances on the Merger of Electrochemistry and Transition Metal Catalysis for Organic Synthesis Malapit, Christian A.; Prater, Matthew B.; Cabrera-Pardo, Jaime R. Chemical Reviews, Vol. 122, Issue 3 https://doi.org/10.1021/acs.chemrev.1c00614	journal	November 2021
Barrier to pyramidal inversion in the tert-butyl radical by electron spin resonance Krusic, P. J.; Meakin, P. Journal of the American Chemical Society, Vol. 98, Issue 1 https://doi.org/10.1021/ja00417a036	journal	January 1976
Photoredox-Catalyzed C–H Functionalization Reactions Holmberg-Douglas, Natalie; Nicewicz, David A. Chemical Reviews, Vol. 122, Issue 2 https://doi.org/10.1021/acs.chemrev.1c00311	journal	September 2021
Advances in Stereoconvergent Catalysis from 2005 to 2015: Transition-Metal-Mediated Stereoablative Reactions, Dynamic Kinetic Resolutions, and Dynamic Kinetic Asymmetric Transformations Bhat, Vikram; Welin, Eric R.; Guo, Xuelei Chemical Reviews, Vol. 117, Issue 5 https://doi.org/10.1021/acs.chemrev.6b00731	journal	February 2017
Transition-Metal Catalysis of Nucleophilic Substitution Reactions: A Radical Alternative to S _N 1 and S _N 2 Processes Fu, Gregory C. ACS Central Science, Vol. 3, Issue 7 https://doi.org/10.1021/acscentsci.7b00212	journal	June 2017
Advances in the E → Z Isomerization of Alkenes Using Small Molecule Photocatalysts Neveselý, Tomáš; Wienhold, Max; Molloy, John J. Chemical Reviews https://doi.org/10.1021/acs.chemrev.1c00324	journal	August 2021
PHOTOCHEMICAL cis-trans-ISOMERIZATION OF SUBSTITUTED STILBENES Schulte-Frohlinde, Dietrich; Blume, Hartwig; Güsten, Hans The Journal of Physical Chemistry, Vol. 66, Issue 12 https://doi.org/10.1021/j100818a039	journal	December 1962
Photosensitized Cis-Trans Isomerization of the Piperylenes Hammond, George S.; Leermakers, Peter A.; Turro, Nicholas J. Journal of the American Chemical Society, Vol. 83, Issue 10 https://doi.org/10.1021/ja01471a045	journal	May 1961
Mechanisms of Photoreactions in Solution. XVIII. Energy Transfer with Nonvertical Transitions Hammond, George S.; Saltiel, Jack. Journal of the American Chemical Society, Vol. 85, Issue 16 https://doi.org/10.1021/ja00899a037	journal	August 1963
Photosensitized Isomerization Involving Saturated Centers Hammond, George S.; Wyatt, Peter.; DeBoer, Charles D. Journal of the American Chemical Society, Vol. 86, Issue 12 https://doi.org/10.1021/ja01066a056	journal	June 1964
Mechanisms of Photochemical Reactions in Solution. XXII. ¹ Photochemical cis-trans Isomerization Hammond, George S.; Saltiel, Jack.; Lamola, Angelo A. Journal of the American Chemical Society, Vol. 86, Issue 16 https://doi.org/10.1021/ja01070a002	journal	August 1964
Metal carbonyl photoassisted cis-trans isomerization of stilbene Gray, Harry B.; Wrighton, Mark; Hammond, G. S. Journal of the American Chemical Society, Vol. 93, Issue 13 https://doi.org/10.1021/ja00742a033	journal	June 1971
Mechanisms of photochemical reactions in solution. LXVII. Energy wastage in photosensitized isomerization of the stilbenes Valentine, Donald; Hammond, George S. Journal of the American Chemical Society, Vol. 94, Issue 10 https://doi.org/10.1021/ja00765a032	journal	May 1972
The case of medium-dependent dual mechanisms for photoisomerization: One-bond-flip and Hula-Twist Liu, R. S. H.; Hammond, G. S. Proceedings of the National Academy of Sciences, Vol. 97, Issue 21 https://doi.org/10.1073/pnas.210323197	journal	October 2000
Examples of Hula-Twist in Photochemicalcis-trans Isomerization Liu, Robert S. H.; Hammond, George S. Chemistry - A European Journal, Vol. 7, Issue 21 https://doi.org/10.1002/1521-3765(20011105)7:21<4536::AID-CHEM4536>3.0.CO;2-N	journal	November 2001
UNUSUAL BEHAVIOUR OF β- tert -ALKYLSTYRENES IN PHOTOSENSITIZED CIS–TRANS ISOMERIZATION. STRUCTURAL EFFECTS ON TRIPLET ENERGY TRANSFER Arai, Tatsuo; Sakuragi, Hirochika; Tokumaru, Katsumi Chemistry Letters, Vol. 9, Issue 3 https://doi.org/10.1246/cl.1980.261	journal	March 1980
Photosensitized cis - trans Isomerization of β-Alkylstyrenes Arai, Tatsuo; Sakuragi, Hirochika; Tokumaru, Katsumi Bulletin of the Chemical Society of Japan, Vol. 55, Issue 7 https://doi.org/10.1246/bcsj.55.2204	journal	July 1982
Novel insights into photoisomerization of olefins Arai, T.; Karatsu, T.; Misawa, H. Pure and Applied Chemistry, Vol. 60, Issue 7 https://doi.org/10.1351/pac198860070989	journal	January 1988
Triplet state Z/E-isomerization of a p-styrylstilbene: a partly adiabatic process Sundahl, Mikael.; Wennerstroem, Olof.; Sandros, Kjell. The Journal of Physical Chemistry, Vol. 94, Issue 17 https://doi.org/10.1021/j100380a037	journal	August 1990
Triplet state 1- and 2-fold cis-trans isomerization of bis(styryl)arenes - balance between diabatic and adiabatic mechanisms Anger, Ingjald; Sundahl, Mikael; Wennerstroem, Olof The Journal of Physical Chemistry, Vol. 96, Issue 17 https://doi.org/10.1021/j100196a034	journal	August 1992
Trans → cis One-way Photoisomerization of an Olefin Substituted with an Indole and a Pyridine Ring. Effect of Intramolecular Hydrogen Bond Arai, Tatsuo; Iwasaki, Takeshi; Tokumaru, Katsumi Chemistry Letters, Vol. 22, Issue 4 https://doi.org/10.1246/cl.1993.691	journal	April 1993
Photochemical one-way adiabatic isomerization of aromatic olefins Arai, Tatsuo.; Tokumaru, Katsumi. Chemical Reviews, Vol. 93, Issue 1 https://doi.org/10.1021/cr00017a002	journal	January 1993
Marked dependence of multiplicity in direct , photoisomerization of a series of methyl cinnamtes on their -substituents Ishigami, Tatsuzo; Nakazato, Kenji; Uehara, Masatoshi Tetrahedron Letters, Vol. 20, Issue 10 https://doi.org/10.1016/S0040-4039(01)93572-5	journal	January 1979
Lewis acid enhancement of photochemical trans .fwdarw. cis isomerization of .alpha.,.beta.-unsaturated esters Lewis, Frederick D.; Oxman, Joe D. Journal of the American Chemical Society, Vol. 103, Issue 24 https://doi.org/10.1021/ja00414a056	journal	December 1981
Selective trans to cis isomerization of alkenes via infrared multiphoton excitation Teng, Peter P.; Weitz, Eric; Lewis, Frederick D. Journal of the American Chemical Society, Vol. 104, Issue 20 https://doi.org/10.1021/ja00384a058	journal	October 1982
Infrared-laser-induced gas-phase isomerization of olefins in the presence of iron pentacarbonyl (Fe(CO)5) Teng, Peter A.; Lewis, Frederick D.; Weitz, Eric The Journal of Physical Chemistry, Vol. 88, Issue 21 https://doi.org/10.1021/j150665a018	journal	October 1984
One-way photoisomerization of cis-stilbene via a cation radical chain mechanism Lewis, Frederick D.; Petisce, James R.; Oxman, Joe D. Journal of the American Chemical Society, Vol. 107, Issue 1 https://doi.org/10.1021/ja00287a037	journal	January 1985
Selective isomerization of alkenes, dienes, and trienes with infrared lasers Lewis, Frederick D.; Weitz, Eric Accounts of Chemical Research, Vol. 18, Issue 6 https://doi.org/10.1021/ar00114a005	journal	June 1985
Infrared multiphoton isomerization reactions of alkenes and dienes Lewis, Frederick D.; Teng, Peter.; Weitz, Eric. Journal of the American Chemical Society, Vol. 108, Issue 11 https://doi.org/10.1021/ja00271a006	journal	May 1986
Lewis-acid catalysis of photochemical reactions. 9. Structure and photoisomerization of (E)- and (Z)-cinnamamides and their Lewis acid complexes Lewis, Frederick D.; Elbert, Jeffrey E.; Upthagrove, Alana L. The Journal of Organic Chemistry, Vol. 56, Issue 2 https://doi.org/10.1021/jo00002a015	journal	January 1991
Lewis acid catalysis of photochemical reactions. 4. Selective isomerization of cinnamic esters Lewis, Frederick D.; Oxman, Joe D.; Gibson, Lester L. Journal of the American Chemical Society, Vol. 108, Issue 11 https://doi.org/10.1021/ja00271a033	journal	May 1986
Lewis acid catalysis of photochemical reactions. 5. Selective isomerization of conjugated butenoic and dienoic esters Lewis, Frederick D.; Howard, Daniel K.; Barancyk, Steven V. Journal of the American Chemical Society, Vol. 108, Issue 11 https://doi.org/10.1021/ja00271a034	journal	May 1986
Lewis-acid catalysis of photochemical reactions. 6. Selective isomerization of .beta.-furylacrylic and urocanic esters Lewis, Frederick D.; Howard, Daniel K.; Oxman, Joe D. Journal of the American Chemical Society, Vol. 108, Issue 19 https://doi.org/10.1021/ja00279a049	journal	September 1986
Singlet-state cis-trans photoisomerization of 1-phenylpropene Lewis, Frederick D.; Bassani, Dario M. Journal of the American Chemical Society, Vol. 115, Issue 16 https://doi.org/10.1021/ja00069a070	journal	August 1993
Molecular Structure and Photochemistry of (E)- and (Z)-2-(2-(2-Pyridyl)ethenyl)indole. A Case of Hydrogen Bond Dependent One-Way Photoisomerization Lewis, Frederick D.; Yoon, Beth A.; Arai, Tatsuo Journal of the American Chemical Society, Vol. 117, Issue 11 https://doi.org/10.1021/ja00116a008	journal	March 1995
Photochemistry of polyenes. IX. Excitation, relaxation, and deactivation of dienes, trienes, and higher polyenes in the vitamin A series in the sensitized isomerization reaction Ramamurthy, V.; Liu, R. S. H. Journal of the American Chemical Society, Vol. 98, Issue 10 https://doi.org/10.1021/ja00426a043	journal	May 1976
Photoisomerization dynamics of stilbenes Waldeck, David H. Chemical Reviews, Vol. 91, Issue 3 https://doi.org/10.1021/cr00003a007	journal	May 1991
X‐ and γ‐Ray‐Induced Radiolytic Isomerization of Solutions of Stilbene Fischer, Ernst; Lehmann, H. P.; Stein, Gabriel The Journal of Chemical Physics, Vol. 45, Issue 11 https://doi.org/10.1063/1.1727436	journal	December 1966
Triplet energy transfer to cis and trans stilbene. A quantum mechanical approach Orlandi, G.; Monti, S.; Barigelletti, F. Chemical Physics, Vol. 52, Issue 3 https://doi.org/10.1016/0301-0104(80)85235-9	journal	November 1980
The triplet state in stilbene cis-trans photoisomerization Saltiel, J.; Chang, D. W. L.; Megarity, E. D. Pure and Applied Chemistry, Vol. 41, Issue 4 https://doi.org/10.1351/pac197541040559	journal	January 1975
Nonvertical triplet excitation transfer to cis- and trans-stilbene Saltiel, Jack; Marchand, Gary R.; Kirkor-Kaminska, Ewa Journal of the American Chemical Society, Vol. 106, Issue 11 https://doi.org/10.1021/ja00323a014	journal	May 1984
Facile Synthesis of Z -Alkenes via Uphill Catalysis Singh, Kamaljeet; Staig, Shannon J.; Weaver, Jimmie D. Journal of the American Chemical Society, Vol. 136, Issue 14 https://doi.org/10.1021/ja5019749	journal	February 2014
Chemical Dynamics in Proteins: The Photoisomerization of Retinal in Bacteriorhodopsin Gai, F. Science, Vol. 279, Issue 5358 https://doi.org/10.1126/science.279.5358.1886	journal	March 1998
Isomerisation of the Visual Chromophore All-trans to 11-cis Retinal O'Leary, Brian; Duke, Brian; Eilers, James E. Nature, Vol. 246, Issue 5429 https://doi.org/10.1038/246166a0	journal	November 1973
Synthetic Control of Retinal Photochemistry and Photophysics in Solution Bassolino, Giovanni; Sovdat, Tina; Liebel, Matz Journal of the American Chemical Society, Vol. 136, Issue 6 https://doi.org/10.1021/ja4121814	journal	January 2014
A Bio-Inspired, Catalytic E → Z Isomerization of Activated Olefins Metternich, Jan B.; Gilmour, Ryan Journal of the American Chemical Society, Vol. 137, Issue 35 https://doi.org/10.1021/jacs.5b07136	journal	August 2015
Flavin-Mediated Visible-Light [2+2] Photocycloaddition of Nitrogen- and Sulfur-Containing Dienes Jirásek, Michael; Straková, Karolína; Neveselý, Tomáš European Journal of Organic Chemistry, Vol. 2017, Issue 15 https://doi.org/10.1002/ejoc.201601377	journal	January 2017
Tailoring flavins for visible light photocatalysis: organocatalytic [2+2] cycloadditions mediated by a flavin derivative and visible light Mojr, Viktor; Svobodová, Eva; Straková, Karolína Chemical Communications, Vol. 51, Issue 60 https://doi.org/10.1039/C5CC01344E	journal	January 2015
Photochemistry of polyenes. III. Preparation of 7-cis-ionyl and ionylidene derivatives and other sterically hindered olefins by one-way sensitized geometric isomerization Ramamurthy, V.; Butt, Y.; Yang, C. The Journal of Organic Chemistry, Vol. 38, Issue 6 https://doi.org/10.1021/jo00946a050	journal	March 1973
Photochemistry of polyenes. VII. Preferred directions of photoisomerization of ionylideneacetaldehyde and the C18-tetraene ketone in the retinal series. Synthesis of the hindered 7-cis isomers Ramamurthy, V.; Liu, R. S. H. Journal of the American Chemical Society, Vol. 96, Issue 17 https://doi.org/10.1021/ja00824a081	journal	August 1974
Preparation of sterically hindered geometric isomers of 7-cis-β-ionyl and β-ionylidene derivatives in the vitamin A series Ramamurthy, V.; Tustin, G.; Yau, C. C. Tetrahedron, Vol. 31, Issue 3 https://doi.org/10.1016/0040-4020(75)85065-4	journal	January 1975
NMR studies of 7--β-ionol and related compounds. Ring-chain conformational preference Ramamurthy, V.; Bopp, T. T.; Liu, R. S. H. Tetrahedron Letters, Vol. 13, Issue 37 https://doi.org/10.1016/S0040-4039(01)94195-4	journal	January 1972
Restricted rotation and ring-chain conformation in hindered 7-cis isomers of retinal and related compounds. A nuclear magnetic resonance study Liu, R. S. H.; Zingoni, Jesmael P.; Kini, Aravinda The Journal of Organic Chemistry, Vol. 48, Issue 25 https://doi.org/10.1021/jo00173a007	journal	December 1983
Photocatalytic E → Z Isomerization of β-Ionyl Derivatives Livingstone, Keith; Tenberge, Marius; Pape, Felix Organic Letters, Vol. 21, Issue 23 https://doi.org/10.1021/acs.orglett.9b03842	journal	November 2019
Visible-Light-Activated Divergent Reactivity of Dienones: Dimerization in Neat Conditions and Regioselective E to Z Isomerization in the Solvent Naskar, Sandip; Roy Chowdhury, Sabyasachi; Mondal, Somrita Organic Letters, Vol. 21, Issue 6 https://doi.org/10.1021/acs.orglett.9b00083	journal	February 2019
Boron-enabled geometric isomerization of alkenes via selective energy-transfer catalysis Molloy, John J.; Schäfer, Michael; Wienhold, Max Science, Vol. 369, Issue 6501 https://doi.org/10.1126/science.abb7235	journal	July 2020
Leveraging the n→π* Interaction in Alkene Isomerization by Selective Energy Transfer Catalysis Neveselý, Tomáš; Molloy, John J.; McLaughlin, Calum Angewandte Chemie International Edition, Vol. 61, Issue 2 https://doi.org/10.1002/anie.202113600	journal	November 2021
Photochemical Alkene Isomerization for the Synthesis of Polysubstituted Furans and Pyrroles under Neutral Conditions Walker, Johannes C. L.; Werrel, Simon; Donohoe, Timothy J. Chemistry – A European Journal, Vol. 25, Issue 57 https://doi.org/10.1002/chem.201903590	journal	September 2019
Sequential Energy Transfer Catalysis: A Cascade Synthesis of Angularly-Fused Dihydrocoumarins Neveselý, Tomáš; Daniliuc, Constantin G.; Gilmour, Ryan Organic Letters, Vol. 21, Issue 23 https://doi.org/10.1021/acs.orglett.9b03882	journal	November 2019
Highly enantioselective protonation of photodienols an unusual substituent effect on the induced chirality Piva, Olivier; Pete, Jean-Pierre Tetrahedron Letters, Vol. 31, Issue 36 https://doi.org/10.1016/S0040-4039(00)97830-4	journal	January 1990
Highly enantioselective photodeconjugation of .alpha.,.beta.-unsaturated esters. Origin of the chiral discrimination Piva, Olivier; Mortezaei, Reza; Henin, Francoise Journal of the American Chemical Society, Vol. 112, Issue 25 https://doi.org/10.1021/ja00181a032	journal	December 1990
Enantiodivergent Prenylation via Deconjugative Isomerization Morack, Tobias; Onneken, Carina; Nakakohara, Hiroshi ACS Catalysis, Vol. 11, Issue 19 https://doi.org/10.1021/acscatal.1c03089	journal	September 2021
Catalytic, contra -Thermodynamic Positional Alkene Isomerization Occhialini, Gino; Palani, Vignesh; Wendlandt, Alison E. Journal of the American Chemical Society, Vol. 144, Issue 1 https://doi.org/10.1021/jacs.1c12043	journal	December 2021
Contra-Thermodynamic Positional Isomerization of Olefins Zhao, Kuo; Knowles, Robert R. Journal of the American Chemical Society, Vol. 144, Issue 1 https://doi.org/10.1021/jacs.1c11681	journal	December 2021
Radical-chain racemisation of tetrahydrofurfuryl acetate under conditions of polarity-reversal catalysis: possible implications for the radical-induced strand cleavage of DNA Cai, Yudong Chemical Communications, Issue 10 https://doi.org/10.1039/a801381k	journal	January 1998
Selective radical-chain epimerisation at CH centres α to oxygen under conditions of polarity-reversal catalysis Dang, Hai-Shan; Roberts, Brian P. Tetrahedron Letters, Vol. 40, Issue 22 https://doi.org/10.1016/S0040-4039(99)00704-2	journal	May 1999
Polarity-reversal catalysis of hydrogen-atom abstraction reactions: concepts and applications in organic chemistry Roberts, Brian P. Chemical Society Reviews, Vol. 28, Issue 1 https://doi.org/10.1039/a804291h	journal	January 1999
Strategy for contra-thermodynamic radical-chain epimerisation of 1,2-diols using polarity-reversal catalysis Dang, Hai-Shan; Roberts, Brian P. Tetrahedron Letters, Vol. 41, Issue 44 https://doi.org/10.1016/S0040-4039(00)01502-1	journal	October 2000
Selective radical-chain epimerisation at electron-rich chiral tertiary C–H centres using thiols as protic polarity-reversal catalysts Dang, Hai-Shan; Roberts, Brian P.; Tocher†, Derek A. Journal of the Chemical Society, Perkin Transactions 1, Issue 19 https://doi.org/10.1039/b103558b	journal	January 2001
Synthesis of rare sugar isomers through site-selective epimerization Wang, Yong; Carder, Hayden M.; Wendlandt, Alison E. Nature, Vol. 578, Issue 7795 https://doi.org/10.1038/s41586-020-1937-1	journal	January 2020
Site-selective carbon–carbon bond formation in unprotected monosaccharides using photoredox catalysis Wan, Ieng Chim (Steven); Witte, Martin D.; Minnaard, Adriaan J. Chemical Communications, Vol. 53, Issue 36 https://doi.org/10.1039/C7CC01416C	journal	January 2017
Site-Selective and Stereoselective C–H Alkylations of Carbohydrates via Combined Diarylborinic Acid and Photoredox Catalysis Dimakos, Victoria; Su, Hsin Y.; Garrett, Graham E. Journal of the American Chemical Society, Vol. 141, Issue 13 https://doi.org/10.1021/jacs.9b01531	journal	March 2019
Site-selective redox isomerizations of furanosides using a combined arylboronic acid/photoredox catalyst system Dimakos, Victoria; Gorelik, Daniel; Su, Hsin Y. Chemical Science, Vol. 11, Issue 6 https://doi.org/10.1039/C9SC05173B	journal	January 2020
A Change from Kinetic to Thermodynamic Control Enables trans-Selective Stereochemical Editing of Vicinal Diols Zhang, Yu-An; Gu, Xin; Wendlandt, Alison E. Journal of the American Chemical Society, Vol. 144, Issue 1 https://doi.org/10.1021/jacs.1c11902	journal	December 2021
Selective Isomerization via Transient Thermodynamic Control: Dynamic Epimerization of trans to cis Diols Oswood, Christian J.; MacMillan, David W. C. Journal of the American Chemical Society, Vol. 144, Issue 1 https://doi.org/10.1021/jacs.1c11552	journal	December 2021
General Light-Mediated, Highly Diastereoselective Piperidine Epimerization: From Most Accessible to Most Stable Stereoisomer Shen, Zican; Walker, Morgan M.; Chen, Shuming Journal of the American Chemical Society, Vol. 143, Issue 1 https://doi.org/10.1021/jacs.0c11911	journal	December 2020
Epimerization of Tertiary Carbon Centers via Reversible Radical Cleavage of Unactivated C(sp³)–H Bonds Wang, Yaxin; Hu, Xiafei; Morales-Rivera, Cristian A. Journal of the American Chemical Society, Vol. 140, Issue 30 https://doi.org/10.1021/jacs.8b05753	journal	July 2018
Catalytic deracemization of chiral allenes by sensitized excitation with visible light Hölzl-Hobmeier, Alena; Bauer, Andreas; Silva, Alexandre Vieira Nature, Vol. 564, Issue 7735 https://doi.org/10.1038/s41586-018-0755-1	journal	December 2018
Photochemical Deracemization of Primary Allene Amides by Triplet Energy Transfer: A Combined Synthetic and Theoretical Study Plaza, Manuel; Großkopf, Johannes; Breitenlechner, Stefan Journal of the American Chemical Society, Vol. 143, Issue 29 https://doi.org/10.1021/jacs.1c05286	journal	July 2021
Photochemically Induced Ring Opening of Spirocyclopropyl Oxindoles: Evidence for a Triplet 1,3‐Diradical Intermediate and Deracemization by a Chiral Sensitizer Li, Xinyao; Kutta, Roger J.; Jandl, Christian Angewandte Chemie International Edition, Vol. 59, Issue 48 https://doi.org/10.1002/anie.202008384	journal	September 2020
Light - driven deracemization enabled by excited - state electron transfer Shin, Nick Y.; Ryss, Jonathan M.; Zhang, Xin Science, Vol. 366, Issue 6463 https://doi.org/10.1126/science.aay2204	journal	October 2019
Photochemical Deracemization at sp³-Hybridized Carbon Centers via a Reversible Hydrogen Atom Transfer Großkopf, Johannes; Plaza, Manuel; Seitz, Antonia Journal of the American Chemical Society, Vol. 143, Issue 50 https://doi.org/10.1021/jacs.1c11266	journal	December 2021
Deracemization through photochemical E / Z isomerization of enamines Huang, Mouxin; Zhang, Long; Pan, Tianrun Science, Vol. 375, Issue 6583 https://doi.org/10.1126/science.abl4922	journal	February 2022
Catalytic α-Deracemization of Ketones Enabled by Photoredox Deprotonation and Enantioselective Protonation Zhang, Chenhao; Gao, Anthony Z.; Nie, Xin Journal of the American Chemical Society, Vol. 143, Issue 33 https://doi.org/10.1021/jacs.1c06637	journal	August 2021
Chemoenzymatic Dynamic Kinetic Resolution: A Powerful Tool for the Preparation of Enantiomerically Pure Alcohols and Amines Verho, Oscar; Bäckvall, Jan-E. Journal of the American Chemical Society, Vol. 137, Issue 12 https://doi.org/10.1021/jacs.5b01031	journal	March 2015
Enzymatic Resolution of Alcohols Coupled with Ruthenium-Catalyzed Racemization of the Substrate Alcohol Larsson, Anna L. E.; Persson, B. Anders; Bäckvall, Jan-E. Angewandte Chemie International Edition in English, Vol. 36, Issue 11 https://doi.org/10.1002/anie.199712111	journal	June 1997
Ruthenium- and Enzyme-Catalyzed Dynamic Kinetic Resolution of Secondary Alcohols Persson, B. Anders; Larsson, Anna L. E.; Le Ray, Mikaël Journal of the American Chemical Society, Vol. 121, Issue 8 https://doi.org/10.1021/ja983819+	journal	February 1999
Thiyl Radical Mediated Racemization of Benzylic Amines Escoubet, Stéphanie; Gastaldi, Stéphane; Vanthuyne, Nicolas European Journal of Organic Chemistry, Vol. 2006, Issue 14 https://doi.org/10.1002/ejoc.200600120	journal	July 2006
Thiyl Radical Mediated Racemization of Nonactivated Aliphatic Amines Escoubet, Stéphanie; Gastaldi, Stéphane; Vanthuyne, Nicolas The Journal of Organic Chemistry, Vol. 71, Issue 19 https://doi.org/10.1021/jo061033l	journal	August 2006
Highly Efficient Photochemically Induced Thiyl Radical-Mediated Racemization of Aliphatic Amines at 30 °C Routaboul, Lucie; Vanthuyne, Nicolas; Gastaldi, Stéphane The Journal of Organic Chemistry, Vol. 73, Issue 2 https://doi.org/10.1021/jo702241y	journal	December 2007
Dynamic Kinetic Resolution of Amines Involving Biocatalysis and in Situ Free Radical Mediated Racemization Gastaldi, Stéphane; Escoubet, Stéphanie; Vanthuyne, Nicolas Organic Letters, Vol. 9, Issue 5 https://doi.org/10.1021/ol063062o	journal	February 2007
Chemoenzymatic Dynamic Kinetic Resolution of Primary Amines Catalyzed by CAL-B at 38–40 °C Poulhès, Florent; Vanthuyne, Nicolas; Bertrand, Michèle P. The Journal of Organic Chemistry, Vol. 76, Issue 17 https://doi.org/10.1021/jo201256w	journal	August 2011
Switching from (R)- to (S)-selective chemoenzymatic DKR of amines involving sulfanyl radical-mediated racemization El Blidi, Lahssen; Vanthuyne, Nicolas; Siri, Didier Organic & Biomolecular Chemistry, Vol. 8, Issue 18 https://doi.org/10.1039/c0ob00054j	journal	January 2010
En Route to (S)-Selective Chemoenzymatic Dynamic Kinetic Resolution of Aliphatic Amines. One-Pot KR/Racemization/KR Sequence Leading to (S)-Amides El Blidi, Lahssen; Nechab, Malek; Vanthuyne, Nicolas The Journal of Organic Chemistry, Vol. 74, Issue 7 https://doi.org/10.1021/jo900074w	journal	March 2009
Enantioselective synthesis of amines by combining photoredox and enzymatic catalysis in a cyclic reaction network Guo, Xingwei; Okamoto, Yasunori; Schreier, Mirjam R. Chemical Science, Vol. 9, Issue 22 https://doi.org/10.1039/C8SC01561A	journal	January 2018
Cooperative asymmetric reactions combining photocatalysis and enzymatic catalysis Litman, Zachary C.; Wang, Yajie; Zhao, Huimin Nature, Vol. 560, Issue 7718 https://doi.org/10.1038/s41586-018-0413-7	journal	August 2018
Static to inducibly dynamic stereocontrol: The convergent use of racemic β-substituted ketones DeHovitz, Jacob S.; Loh, Yong Yao; Kautzky, Jacob A. Science, Vol. 369, Issue 6507 https://doi.org/10.1126/science.abc9909	journal	August 2020
Photoredox Activation for the Direct -Arylation of Ketones and Aldehydes Pirnot, M. T.; Rankic, D. A.; Martin, D. B. C. Science, Vol. 339, Issue 6127 https://doi.org/10.1126/science.1232993	journal	March 2013

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