Enantioselective Intramolecular Allylic Substitution via Synergistic Palladium/Chiral Phosphoric Acid Catalysis: Insight into Stereoinduction through Statistical Modeling

Tsai, Cheng‐Che; Sandford, Christopher; Wu, Tao; Chen, Buyun; Sigman, Matthew S.; Toste, F. Dean

doi:10.1002/anie.202006237

Title: Enantioselective Intramolecular Allylic Substitution via Synergistic Palladium/Chiral Phosphoric Acid Catalysis: Insight into Stereoinduction through Statistical Modeling

Journal Article · Tue May 26 00:00:00 EDT 2020 · Angewandte Chemie (International Edition)

DOI:https://doi.org/10.1002/anie.202006237· OSTI ID:1984237

Tsai, Cheng‐Che ^[1];

^[2]; Wu, Tao ^[3]; Chen, Buyun ^[3];

^[2];

^[3]

Univ. of California, Berkeley, CA (United States); Tunghai University (Taiwan)
Univ. of Utah, Salt Lake City, UT (United States)
Univ. of California, Berkeley, CA (United States)

The mode of asymmetric induction in an enantioselective intramolecular allylic substitution reaction catalyzed by a combination of palladium and a chiral phosphoric acid was investigated by a combined experimental and statistical modeling approach. Experiments to probe nonlinear effects, the reactivity of deuterium-labeled substrates, and control experiments revealed that nucleophilic attack to the π-allylpalladium intermediate is the enantio-determining step, in which the chiral phosphate anion is involved in stereoinduction. Here, using multivariable linear regression analysis, we determined that multiple noncovalent interactions with the chiral environment of the phosphate anion are integral to enantiocontrol in the transition state. The synthetic protocol to form chiral pyrrolidines was further applied to the asymmetric construction of C-O bonds at fully substituted carbon centers in the synthesis of chiral 2,2-disubstituted benzomorpholines.

View Accepted Manuscript (DOE)

Cite

Export

Save

Research Organization:: Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES). Chemical Sciences, Geosciences & Biosciences Division (CSGB); National Institutes of Health (NIH); National Science Foundation (NSF)

Grant/Contract Number:: AC02-05CH11231; R35 GM118190; GM121383; ACI-1548562

OSTI ID:: 1984237

Journal Information:: Angewandte Chemie (International Edition), Vol. 59, Issue 34; ISSN 1433-7851

Publisher:: WileyCopyright Statement

Country of Publication:: United States

Language:: English

References (81)

Tsuji-Trost Reaction of Non-Derivatized Allylic Alcohols Akkarasamiyo, Sunisa; Sawadjoon, Supaporn; Orthaber, Andreas Chemistry - A European Journal, Vol. 24, Issue 14 https://doi.org/10.1002/chem.201705164	journal	January 2018
Recent Advances in First-Row Transition Metal/Chiral Phosphoric Acid Combined Catalysis Fang, Gui-Chun; Cheng, Yong-Feng; Yu, Zhang-Long Topics in Current Chemistry, Vol. 377, Issue 5 https://doi.org/10.1007/s41061-019-0249-0	journal	August 2019
Pd-Catalyzed Asymmetric Allylic Alkylation of Pyrazol-5-ones with Allylic Alcohols: The Role of the Chiral Phosphoric Acid in C–O Bond Cleavage and Stereocontrol Tao, Zhong-Lin; Zhang, Wen-Quan; Chen, Dian-Feng Journal of the American Chemical Society, Vol. 135, Issue 25 https://doi.org/10.1021/ja402740q	journal	June 2013
Enantioselective Construction of Tertiary C–O Bond via Allylic Substitution of Vinylethylene Carbonates with Water and Alcohols Khan, Ajmal; Khan, Sardaraz; Khan, Ijaz Journal of the American Chemical Society, Vol. 139, Issue 31 https://doi.org/10.1021/jacs.7b04759	journal	August 2017
Asymmetric γ-Allylation of α,β-Unsaturated Aldehydes by Combined Organocatalysis and Transition-Metal Catalysis Naesborg, Line; Halskov, Kim Søholm; Tur, Fernando Angewandte Chemie, Vol. 127, Issue 35 https://doi.org/10.1002/ange.201504749	journal	July 2015
Cooperative Transition-Metal and Chiral Brønsted Acid Catalysis: Enantioselective Hydrogenation of Imines To Form Amines Zhou, Shaolin; Fleischer, Steffen; Junge, Kathrin Angewandte Chemie, Vol. 123, Issue 22 https://doi.org/10.1002/ange.201100878	journal	April 2011
Chiral Copper(II) Phosphate Catalyzed Enantioselective Synthesis of Isochromene Derivatives by Sequential Intramolecular Cyclization and Asymmetric Transfer Hydrogenation ofo-Alkynylacetophenones Saito, Kodai; Kajiwara, Yuki; Akiyama, Takahiko Angewandte Chemie International Edition, Vol. 52, Issue 50 https://doi.org/10.1002/anie.201308303	journal	November 2013
A Mechanistic Analysis of the Palladium‐Catalyzed Formation of Branched Allylic Amines Reveals the Origin of the Regio‐ and Enantioselectivity through a Unique Inner‐Sphere Pathway Hu, Lingfei; Cai, Aijie; Wu, Zhenzhen Angewandte Chemie International Edition, Vol. 58, Issue 41 https://doi.org/10.1002/anie.201907375	journal	September 2019
Wavefunction methods for noncovalent interactions: Noncovalent interactions Hohenstein, Edward G.; Sherrill, C. David Wiley Interdisciplinary Reviews: Computational Molecular Science, Vol. 2, Issue 2 https://doi.org/10.1002/wcms.84	journal	July 2011
Palladium-Catalyzed Asymmetric Aminohydroxylation of 1,3-Dienes Shen, Hong-Cheng; Wu, Yu-Feng; Zhang, Ying Angewandte Chemie International Edition, Vol. 57, Issue 9 https://doi.org/10.1002/anie.201712350	journal	February 2018
Unusual Effects in the Pd-Catalyzed Asymmetric Allylic Alkylations: Synthesis of Chiral Chromans Trost, Barry M.; Shen, Hong C.; Dong, Li Journal of the American Chemical Society, Vol. 125, Issue 31 https://doi.org/10.1021/ja036052g	journal	July 2003
Water Enables Direct Use of Allyl Alcohol for Tsuji−Trost Reaction without Activators Kinoshita, Hidenori; Shinokubo, Hiroshi; Oshima, Koichiro Organic Letters, Vol. 6, Issue 22 https://doi.org/10.1021/ol048207a	journal	October 2004
Nichtlineare Effekte in der asymmetrischen Katalyse Satyanarayana, Tummanapalli; Abraham, Susan; Kagan, Henri B. Angewandte Chemie, Vol. 121, Issue 3 https://doi.org/10.1002/ange.200705241	journal	January 2009
Cooperative Catalysis by Palladium and a Chiral Phosphoric Acid: Enantioselective Amination of Racemic Allylic Alcohols Banerjee, Debasis; Junge, Kathrin; Beller, Matthias Angewandte Chemie, Vol. 126, Issue 48 https://doi.org/10.1002/ange.201405511	journal	October 2014
Enantioselective Synthesis of Fluoro–Dihydroquinazolones and −Benzooxazinones by Fluorination-Initiated Asymmetric Cyclization Reactions Hiramatsu, Kenichi; Honjo, Takashi; Rauniyar, Vivek ACS Catalysis, Vol. 6, Issue 1 https://doi.org/10.1021/acscatal.5b02182	journal	December 2015
Disparate Catalytic Scaffolds for Atroposelective Cyclodehydration Kwon, Yongseok; Li, Junqi; Reid, Jolene P. Journal of the American Chemical Society, Vol. 141, Issue 16 https://doi.org/10.1021/jacs.9b01911	journal	March 2019
A Doubly Axially Chiral Phosphoric Acid Catalyst for the Asymmetric Tandem Oxyfluorination of Enamides Honjo, Takashi; Phipps, Robert J.; Rauniyar, Vivek Angewandte Chemie, Vol. 124, Issue 38 https://doi.org/10.1002/ange.201205383	journal	August 2012
Harnessing Noncovalent Interactions in Dual-Catalytic Enantioselective Heck–Matsuda Arylation Reddi, Yernaidu; Tsai, Cheng-Che; Avila, Carolina M. Journal of the American Chemical Society, Vol. 141, Issue 2 https://doi.org/10.1021/jacs.8b11062	journal	December 2018
Chemo- and Regioselectivity-Tunable Pd-Catalyzed Allylic Alkylation of Imines Chen, Jian-Ping; Peng, Qian; Lei, Bai-Lin Journal of the American Chemical Society, Vol. 133, Issue 36 https://doi.org/10.1021/ja2039503	journal	September 2011
Palladium(II)-Catalyzed Enantioselective Synthesis of 2-Vinyl Oxygen Heterocycles Cannon, Jeffrey S.; Olson, Angela C.; Overman, Larry E. The Journal of Organic Chemistry, Vol. 77, Issue 4 https://doi.org/10.1021/jo202553a	journal	February 2012
Palladium-Catalyzed Asymmetric Aminohydroxylation of 1,3-Dienes Shen, Hong-Cheng; Wu, Yu-Feng; Zhang, Ying Angewandte Chemie, Vol. 130, Issue 9 https://doi.org/10.1002/ange.201712350	journal	February 2018
Organocatalytic Activation of the Leaving Group in the Intramolecular Asymmetric S_N2′ Reaction Kuroda, Yusuke; Harada, Shingo; Oonishi, Akinori Angewandte Chemie, Vol. 127, Issue 28 https://doi.org/10.1002/ange.201502831	journal	May 2015
Transition metal catalyzed nucleophilic allylic substitution: activation of allylic alcohols via π-allylic species Sundararaju, Basker; Achard, Mathieu; Bruneau, Christian Chemical Society Reviews, Vol. 41, Issue 12 https://doi.org/10.1039/c2cs35024f	journal	January 2012
Chiral Primary Amine/Palladium Dual Catalysis for Asymmetric Allylic Alkylation of β-Ketocarbonyl Compounds with Allylic Alcohols Zhou, Han; Zhang, Long; Xu, Changming Angewandte Chemie, Vol. 127, Issue 43 https://doi.org/10.1002/ange.201505946	journal	September 2015
Conformational Dynamics in Asymmetric Catalysis: Is Catalyst Flexibility a Design Element? Crawford, Jennifer; Sigman, Matthew Synthesis, Vol. 51, Issue 05 https://doi.org/10.1055/s-0037-1611636	journal	January 2019
Origin of Inversion versus Retention in the Oxidative Addition of 3-Chloro-cyclopentene to Pd(0)L_n Wolf, Larry M.; Thiel, Walter The Journal of Organic Chemistry, Vol. 79, Issue 24 https://doi.org/10.1021/jo5020068	journal	October 2014
Levels of symmetry adapted perturbation theory (SAPT). I. Efficiency and performance for interaction energies Parker, Trent M.; Burns, Lori A.; Parrish, Robert M. The Journal of Chemical Physics, Vol. 140, Issue 9 https://doi.org/10.1063/1.4867135	journal	March 2014
Cooperative Transition-Metal and Chiral Brønsted Acid Catalysis: Enantioselective Hydrogenation of Imines To Form Amines Zhou, Shaolin; Fleischer, Steffen; Junge, Kathrin Angewandte Chemie International Edition, Vol. 50, Issue 22 https://doi.org/10.1002/anie.201100878	journal	April 2011
The Development of Double Axially Chiral Phosphoric Acids and Their Catalytic Transfer Hydrogenation of Quinolines Guo, Qun-Sheng; Du, Da-Ming; Xu, Jiaxi Angewandte Chemie, Vol. 120, Issue 4 https://doi.org/10.1002/ange.200703925	journal	January 2008
Enantioselective Heck-Matsuda Arylations through Chiral Anion Phase-Transfer of Aryl Diazonium Salts Avila, Carolina M.; Patel, Jigar S.; Reddi, Yernaidu Angewandte Chemie, Vol. 129, Issue 21 https://doi.org/10.1002/ange.201702107	journal	April 2017
Enantio- and Diastereodivergent Dual Catalysis: -Allylation of Branched Aldehydes Krautwald, S.; Sarlah, D.; Schafroth, M. A. Science, Vol. 340, Issue 6136 https://doi.org/10.1126/science.1237068	journal	May 2013
Synthesis of Chiral Chromans by the Pd-Catalyzed Asymmetric Allylic Alkylation (AAA): Scope, Mechanism, and Applications Trost, Barry M.; Shen, Hong C.; Dong, Li Journal of the American Chemical Society, Vol. 126, Issue 38 https://doi.org/10.1021/ja048078t	journal	September 2004
Exploring Nature and Predicting Strength of Hydrogen Bonds: A Correlation Analysis Between Atoms‐in‐Molecules Descriptors, Binding Energies, and Energy Components of Symmetry‐Adapted Perturbation Theory Emamian, Saeedreza; Lu, Tian; Kruse, Holger Journal of Computational Chemistry, Vol. 40, Issue 32 https://doi.org/10.1002/jcc.26068	journal	September 2019
Phase-transfer-catalysed asymmetric synthesis of 2,2-disubstituted 1,4-benzoxazin-3-ones Pawliczek, Martin; Shimazaki, Yuto; Kimura, Hidenori Chemical Communications, Vol. 54, Issue 51 https://doi.org/10.1039/C8CC03635G	journal	January 2018
A Doubly Axially Chiral Phosphoric Acid Catalyst for the Asymmetric Tandem Oxyfluorination of Enamides Honjo, Takashi; Phipps, Robert J.; Rauniyar, Vivek Angewandte Chemie International Edition, Vol. 51, Issue 38 https://doi.org/10.1002/anie.201205383	journal	August 2012
Gold‐Catalyzed Asymmetric Allylic Substitution of Free Alcohols: An Enantioselective Approach to Chiral Chromans with Quaternary Stereocenters for the Synthesis of Vitamin E and Analogues Uria, Uxue; Vila, Carlos; Lin, Ming‐Yuan Chemistry – A European Journal, Vol. 20, Issue 43 https://doi.org/10.1002/chem.201403768	journal	September 2014
Enantioselective Heck-Matsuda Arylations through Chiral Anion Phase-Transfer of Aryl Diazonium Salts Avila, Carolina M.; Patel, Jigar S.; Reddi, Yernaidu Angewandte Chemie International Edition, Vol. 56, Issue 21 https://doi.org/10.1002/anie.201702107	journal	April 2017
Enantioselective Oxidative Homocoupling and Cross-Coupling of 2-Naphthols Catalyzed by Chiral Iron Phosphate Complexes Narute, Sachin; Parnes, Regev; Toste, F. Dean Journal of the American Chemical Society, Vol. 138, Issue 50 https://doi.org/10.1021/jacs.6b11198	journal	December 2016
Asymmetric Allylation of Furfural Derivatives: Synergistic Effect of Chiral Ligand and Organocatalyst on Stereochemical Control Su, Yong-Liang; Han, Zhi-Yong; Li, Yu-Hui ACS Catalysis, Vol. 7, Issue 11 https://doi.org/10.1021/acscatal.7b02667	journal	October 2017
Organocatalytic Activation of the Leaving Group in the Intramolecular Asymmetric S_N2′ Reaction Kuroda, Yusuke; Harada, Shingo; Oonishi, Akinori Angewandte Chemie International Edition, Vol. 54, Issue 28 https://doi.org/10.1002/anie.201502831	journal	May 2015
A Dual-Catalytic Strategy To Direct Asymmetric Radical Aminotrifluoromethylation of Alkenes Lin, Jin-Shun; Dong, Xiao-Yang; Li, Tao-Tao Journal of the American Chemical Society, Vol. 138, Issue 30 https://doi.org/10.1021/jacs.6b04077	journal	July 2016
Pursuit of Noncovalent Interactions for Strategic Site-Selective Catalysis Toste, F. Dean; Sigman, Matthew S.; Miller, Scott J. Accounts of Chemical Research, Vol. 50, Issue 3 https://doi.org/10.1021/acs.accounts.6b00613	journal	March 2017
Importance of Ligand Exchanges in Pd(II)-Brønsted Acid Cooperative Catalytic Approach to Spirocyclic Rings Jindal, Garima; Sunoj, Raghavan B. Journal of the American Chemical Society, Vol. 136, Issue 45 https://doi.org/10.1021/ja5076629	journal	November 2014
Chiral Primary Amine/Palladium Dual Catalysis for Asymmetric Allylic Alkylation of β-Ketocarbonyl Compounds with Allylic Alcohols Zhou, Han; Zhang, Long; Xu, Changming Angewandte Chemie International Edition, Vol. 54, Issue 43 https://doi.org/10.1002/anie.201505946	journal	September 2015
Deciphering the Origin of Stereoinduction in Cooperative Asymmetric Catalysis Involving Pd(II) and a Chiral Brønsted Acid Jindal, Garima; Sunoj, Raghavan B. Organic Letters, Vol. 17, Issue 12 https://doi.org/10.1021/acs.orglett.5b00860	journal	June 2015
Chiral Counteranions in Asymmetric Transition-Metal Catalysis: Highly Enantioselective Pd/Brønsted Acid-Catalyzed Direct α-Allylation of Aldehydes Mukherjee, Santanu; List, Benjamin Journal of the American Chemical Society, Vol. 129, Issue 37 https://doi.org/10.1021/ja074678r	journal	September 2007
The Development of Double Axially Chiral Phosphoric Acids and Their Catalytic Transfer Hydrogenation of Quinolines Guo, Qun-Sheng; Du, Da-Ming; Xu, Jiaxi Angewandte Chemie International Edition, Vol. 47, Issue 4 https://doi.org/10.1002/anie.200703925	journal	January 2008
Palladium Catalyzed Kinetic and Dynamic Kinetic Asymmetric Transformations of γ-Acyloxybutenolides. Enantioselective Total Synthesis of (+)-Aflatoxin B₁ and B₂_a Trost, Barry M.; Toste, F. Dean Journal of the American Chemical Society, Vol. 125, Issue 10 https://doi.org/10.1021/ja020988s	journal	February 2003
Predictive and mechanistic multivariate linear regression models for reaction development Santiago, Celine B.; Guo, Jing-Yao; Sigman, Matthew S. Chemical Science, Vol. 9, Issue 9 https://doi.org/10.1039/C7SC04679K	journal	January 2018
A Powerful Chiral Counterion Strategy for Asymmetric Transition Metal Catalysis Hamilton, G. L.; Kang, E. J.; Mba, M. Science, Vol. 317, Issue 5837 https://doi.org/10.1126/science.1145229	journal	July 2007
Direct Asymmetric α-Allylation of Aldehydes with Simple Allylic Alcohols Enabled by the Concerted Action of Three Different Catalysts Jiang, Gaoxi; List, Benjamin Angewandte Chemie International Edition, Vol. 50, Issue 40 https://doi.org/10.1002/anie.201103263	journal	September 2011
Parametrization of Non-covalent Interactions for Transition State Interrogation Applied to Asymmetric Catalysis Orlandi, Manuel; Coelho, Jaime A. S.; Hilton, Margaret J. Journal of the American Chemical Society, Vol. 139, Issue 20 https://doi.org/10.1021/jacs.7b02311	journal	May 2017
The Reaction Mechanism of the Enantioselective Tsuji Allylation: Inner-Sphere and Outer-Sphere Pathways, Internal Rearrangements, and Asymmetric C–C Bond Formation Keith, John A.; Behenna, Douglas C.; Sherden, Nathaniel Journal of the American Chemical Society, Vol. 134, Issue 46 https://doi.org/10.1021/ja306860n	journal	November 2012
Novel syn oxidative addition of allylic halides to olefin complexes of palladium(0) and platinum(0) Kurosawa, Hideo; Kajimaru, Hiroshi; Ogoshi, Sensuke Journal of the American Chemical Society, Vol. 114, Issue 22 https://doi.org/10.1021/ja00048a011	journal	October 1992
Enantioselective Allenoate-Claisen Rearrangement Using Chiral Phosphate Catalysts Miró, Javier; Gensch, Tobias; Ellwart, Mario Journal of the American Chemical Society, Vol. 142, Issue 13 https://doi.org/10.1021/jacs.0c01637	journal	March 2020
Chiral Brønsted acid-catalyzed intramolecular S_N2′ reaction for enantioselective construction of a quaternary stereogenic center Shimizu, Masahiro; Kikuchi, Jun; Kondoh, Azusa Chemical Science, Vol. 9, Issue 26 https://doi.org/10.1039/C8SC01942H	journal	January 2018
Rational design of 6-(2,4-diaminopyrimidinyl)-1,4-benzoxazin-3-ones as small molecule renin inhibitors Powell, Noel A.; Ciske, Fred L.; Cai, Cuiman Bioorganic & Medicinal Chemistry, Vol. 15, Issue 17 https://doi.org/10.1016/j.bmc.2007.05.069	journal	September 2007
Palladium/N-heterocyclic carbene catalysed regio and diastereoselective reaction of ketones with allyl reagents via inner-sphere mechanism Bai, Da-Chang; Yu, Fei-Le; Wang, Wan-Ying Nature Communications, Vol. 7, Issue 1 https://doi.org/10.1038/ncomms11806	journal	June 2016
Complete Field Guide to Asymmetric BINOL-Phosphate Derived Brønsted Acid and Metal Catalysis: History and Classification by Mode of Activation; Brønsted Acidity, Hydrogen Bonding, Ion Pairing, and Metal Phosphates Parmar, Dixit; Sugiono, Erli; Raja, Sadiya Chemical Reviews, Vol. 114, Issue 18 https://doi.org/10.1021/cr5001496	journal	September 2014
Isomerization of (.pi.-allyl)palladium complexes via nucleophilic displacement by palladium(0). A common mechanism in palladium(0)-catalyzed allylic substitution Granberg, Kenneth L.; Baeckvall, Jan E. Journal of the American Chemical Society, Vol. 114, Issue 17 https://doi.org/10.1021/ja00043a034	journal	August 1992
Origin of stereoselectivity in the amination of alcohols using cooperative asymmetric dual catalysis involving chiral counter-ions Tribedi, Soumi; Hadad, Christopher M.; Sunoj, Raghavan B. Chemical Science, Vol. 9, Issue 28 https://doi.org/10.1039/C8SC01433G	journal	January 2018
Chiral Brønsted Acid-Catalyzed Formal α-Vinylation of Cyclopentanones for the Enantioselective Construction of Quaternary Carbon Centers Kayal, Satavisha; Kikuchi, Jun; Shimizu, Masahiro ACS Catalysis, Vol. 9, Issue 8 https://doi.org/10.1021/acscatal.9b01780	journal	June 2019
Chiral Copper(II) Phosphate Catalyzed Enantioselective Synthesis of Isochromene Derivatives by Sequential Intramolecular Cyclization and Asymmetric Transfer Hydrogenation ofo-Alkynylacetophenones Saito, Kodai; Kajiwara, Yuki; Akiyama, Takahiko Angewandte Chemie, Vol. 125, Issue 50 https://doi.org/10.1002/ange.201308303	journal	November 2013
A Mechanistic Analysis of the Palladium‐Catalyzed Formation of Branched Allylic Amines Reveals the Origin of the Regio‐ and Enantioselectivity through a Unique Inner‐Sphere Pathway Hu, Lingfei; Cai, Aijie; Wu, Zhenzhen Angewandte Chemie, Vol. 131, Issue 41 https://doi.org/10.1002/ange.201907375	journal	September 2019
Cu(I)-Catalyzed Diamination of Conjugated Olefins with Tunable Anionic Counterions. A Possible Approach to Asymmetric Diamination Zhao, Baoguo; Du, Haifeng; Shi, Yian The Journal of Organic Chemistry, Vol. 74, Issue 21 https://doi.org/10.1021/jo901685c	journal	October 2009
Asymmetric γ-Allylation of α,β-Unsaturated Aldehydes by Combined Organocatalysis and Transition-Metal Catalysis Naesborg, Line; Halskov, Kim Søholm; Tur, Fernando Angewandte Chemie International Edition, Vol. 54, Issue 35 https://doi.org/10.1002/anie.201504749	journal	July 2015
Synthesis of Chiral 1,4-Benzodioxanes and Chromans by Enantioselective Palladium-Catalyzed Alkene Aryloxyarylation Reactions Hu, Naifu; Li, Ke; Wang, Zheng Angewandte Chemie International Edition, Vol. 55, Issue 16 https://doi.org/10.1002/anie.201600379	journal	March 2016
Enantioconvergent Nucleophilic Substitution Reaction of Racemic Alkyne–Dicobalt Complex (Nicholas Reaction) Catalyzed by Chiral Brønsted Acid Terada, Masahiro; Ota, Yusuke; Li, Feng Journal of the American Chemical Society, Vol. 138, Issue 34 https://doi.org/10.1021/jacs.6b05948	journal	August 2016
Transition metal-catalyzed allylic substitution reactions with unactivated allylic substrates Butt, Nicholas A.; Zhang, Wanbin Chemical Society Reviews, Vol. 44, Issue 22 https://doi.org/10.1039/C5CS00144G	journal	January 2015
Cooperative Catalysis by Palladium and a Chiral Phosphoric Acid: Enantioselective Amination of Racemic Allylic Alcohols Banerjee, Debasis; Junge, Kathrin; Beller, Matthias Angewandte Chemie International Edition, Vol. 53, Issue 48 https://doi.org/10.1002/anie.201405511	journal	October 2014
Iron/Brønsted Acid Catalyzed Asymmetric Hydrogenation: Mechanism and Selectivity-Determining Interactions Hopmann, Kathrin H. Chemistry - A European Journal, Vol. 21, Issue 28 https://doi.org/10.1002/chem.201500602	journal	June 2015
Direkte asymmetrische α-Allylierung von Aldehyden mit Allyalkoholen, ermöglicht durch das Zusammenwirken dreier Katalysatoren Jiang, Gaoxi; List, Benjamin Angewandte Chemie, Vol. 123, Issue 40 https://doi.org/10.1002/ange.201103263	journal	September 2011
Mechanism of the Cobalt Oxazoline Palladacycle (COP)-Catalyzed Asymmetric Synthesis of Allylic Esters Cannon, Jeffrey S.; Kirsch, Stefan F.; Overman, Larry E. Journal of the American Chemical Society, Vol. 132, Issue 43 https://doi.org/10.1021/ja106688j	journal	October 2010
Mechanistic Insights on Cooperative Asymmetric Multicatalysis Using Chiral Counterions Jindal, Garima; Sunoj, Raghavan B. The Journal of Organic Chemistry, Vol. 79, Issue 16 https://doi.org/10.1021/jo501322v	journal	July 2014
Iridium-Catalyzed Asymmetric Synthesis of Functionally Rich Molecules Enabled by (Phosphoramidite,Olefin) Ligands Rössler, Simon L.; Petrone, David A.; Carreira, Erick M. Accounts of Chemical Research, Vol. 52, Issue 9 https://doi.org/10.1021/acs.accounts.9b00209	journal	June 2019
Mechanistic Insights into Asymmetric C–H Insertion Cooperatively Catalyzed by a Dirhodium(II) Complex and Chiral Phosphoric Acid Liu, Hui; Duan, Jun-Xin; Qu, Deyu Organometallics, Vol. 35, Issue 11 https://doi.org/10.1021/acs.organomet.6b00283	journal	May 2016
Synthesis of Chiral 1,4-Benzodioxanes and Chromans by Enantioselective Palladium-Catalyzed Alkene Aryloxyarylation Reactions Hu, Naifu; Li, Ke; Wang, Zheng Angewandte Chemie, Vol. 128, Issue 16 https://doi.org/10.1002/ange.201600379	journal	March 2016
Nonlinear Effects in Asymmetric Catalysis Satyanarayana, Tummanapalli; Abraham, Susan; Kagan, Henri B. Angewandte Chemie International Edition, Vol. 48, Issue 3 https://doi.org/10.1002/anie.200705241	journal	January 2009
A data-intensive approach to mechanistic elucidation applied to chiral anion catalysis Milo, A.; Neel, A. J.; Toste, F. D. Science, Vol. 347, Issue 6223 https://doi.org/10.1126/science.1261043	journal	February 2015
Asymmetric α-Allylation of α-Substituted β-Ketoesters with Allyl Alcohols Yoshida, Masanori The Journal of Organic Chemistry, Vol. 82, Issue 23 https://doi.org/10.1021/acs.joc.7b02188	journal	October 2017
Enantioselective 1,1-Arylborylation of Alkenes: Merging Chiral Anion Phase Transfer with Pd Catalysis Nelson, Hosea M.; Williams, Brett D.; Miró, Javier Journal of the American Chemical Society, Vol. 137, Issue 9 https://doi.org/10.1021/jacs.5b00344	journal	February 2015

Similar Records

Enantioselective C–H Amination Catalyzed by Nickel Iminyl Complexes Supported by Anionic Bisoxazoline (BOX) Ligands

Journal Article · Mon Jan 04 00:00:00 EST 2021 · Journal of the American Chemical Society · OSTI ID:1984237

Dong, Yuyang; Lund, Colton J.; Porter, Gerard J.; +4 more

Enantioselective Allenoate-Claisen Rearrangement Using Chiral Phosphate Catalysts

Journal Article · Tue Mar 17 00:00:00 EDT 2020 · Journal of the American Chemical Society · OSTI ID:1984237

Miró, Javier; Gensch, Tobias; Ellwart, Mario; +4 more

Bisdiamidophosphite with a bisoxazoline moiety in palladium-catalyzed enantioselective allylation

Journal Article · Mon Jul 15 00:00:00 EDT 2019 · Russian Chemical Bulletin · OSTI ID:1984237

Zheglov, S. V.; Gavrilov, V. K.; Firsin, I. D.; +1 more

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
allylic substitution
asymmetric catalysis
noncovalent interactions
palladium
statistical modeling

Title: Enantioselective Intramolecular Allylic Substitution via Synergistic Palladium/Chiral Phosphoric Acid Catalysis: Insight into Stereoinduction through Statistical Modeling

Citation Formats

References (81)

Similar Records

Related Subjects