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; Chen, Di; Li, Hao; Liu, Qing -Rong; Ding, Chang -Hua; Chen, Bo; Hou, Xue -Long

doi:10.1038/ncomms11806

Title: Palladium/N-heterocyclic carbene catalysed regio and diastereoselective reaction of ketones with allyl reagents via inner-sphere mechanism

Journal Article · Fri Jun 10 00:00:00 EDT 2016 · Nature Communications

DOI:https://doi.org/10.1038/ncomms11806· OSTI ID:1287338

Bai, Da -Chang ^[1]; Yu, Fei -Le ^[1]; Wang, Wan -Ying ^[1]; Chen, Di ^[1]; Li, Hao ^[1]; Liu, Qing -Rong ^[1]; Ding, Chang -Hua ^[1];

^[2];

^[3]

Chinese Academy of Sciences, Shanghai (China). State Key Laboratory of Organometallic Chemistry, Shanghai Instit. of Organic Chemistry
Cornell University, Ithaca, NY (United States). Dept. of Chemistry and Chemical Biology, Baker Laboratory
Chinese Academy of Sciences, Shanghai (China). State Key Laboratory of Organometallic Chemistry, Shanghai Instit. of Organic Chemistry and Shanghai Hong Kong Joint Laboratory in Chemical Synthesis

The palladium-catalysed allylic substitution reaction is one of the most important reactions in transition-metal catalysis and has been well-studied in the past decades. Most of the reactions proceed through an outer-sphere mechanism, affording linear products when monosubstituted allyl reagents are used. Here, we report an efficient Palladium-catalysed protocol for reactions of beta-substituted ketones with monosubstituted allyl substrates, simply by using N-heterocyclic carbene as ligand, leading to branched products with up to three contiguous stereocentres in a (syn, anti)-mode with excellent regio and diastereoselectivities. The scope of the protocol in organic synthesis has been examined preliminarily. As a result, mechanistic studies by both experiments and density functional theory ( DFT) calculations reveal that the reaction proceeds via an inner-sphere mechanism-nucleophilic attack of enolate oxygen on Palladium followed by C-C bond-forming [3,3']-reductive elimination.

View Accepted Manuscript (DOE)

Cite

Export

Save

Research Organization:: Chinese Academy of Sciences, Shanghai (China); Energy Frontier Research Centers (EFRC) (United States). Energy Frontier Research in Extreme Environments (EFree)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES)

Grant/Contract Number:: SC0001057

OSTI ID:: 1287338

Journal Information:: Nature Communications, Vol. 7; ISSN 2041-1723

Publisher:: Nature Publishing GroupCopyright Statement

Country of Publication:: United States

Language:: English

Citation Metrics:

Cited by: 50 works

Citation information provided by
Web of Science

References (71)

Multinuclear Catalyst for Copper-Catalyzed Asymmetric Conjugate Addition of Organozinc Reagents Endo, Kohei; Ogawa, Mika; Shibata, Takanori Angewandte Chemie International Edition, Vol. 49, Issue 13 https://doi.org/10.1002/anie.200906839	journal	February 2010
Congested C–C Bonds by Pd-Catalyzed Enantioselective Allyl–Allyl Cross-Coupling, a Mechanism-Guided Solution Ardolino, Michael J.; Morken, James P. Journal of the American Chemical Society, Vol. 136, Issue 19 https://doi.org/10.1021/ja502280w	journal	April 2014
Aiming for the Ideal Synthesis Gaich, Tanja; Baran, Phil S. The Journal of Organic Chemistry, Vol. 75, Issue 14 https://doi.org/10.1021/jo1006812	journal	July 2010
Graphene-Based Photocatalysts for Solar-Fuel Generation Xiang, Quanjun; Cheng, Bei; Yu, Jiaguo Angewandte Chemie International Edition, Vol. 54, Issue 39 https://doi.org/10.1002/anie.201411096	journal	June 2015
Enyne Metathesis (Enyne Bond Reorganization) Diver, Steven T.; Giessert, Anthony J. Chemical Reviews, Vol. 104, Issue 3 https://doi.org/10.1021/cr020009e	journal	March 2004
Pd-Catalyzed Enantioselective Allyl−Allyl Cross-Coupling Zhang, Ping; Brozek, Laura A.; Morken, James P. Journal of the American Chemical Society, Vol. 132, Issue 31 https://doi.org/10.1021/ja105161f	journal	August 2010
Transition-Metal-Catalyzed Allylic Substitution Reactions: Stereoselective Construction of α- and β-Substituted Carbonyl Compounds Oliver, Samuel; Evans, P. Synthesis, Vol. 45, Issue 23 https://doi.org/10.1055/s-0033-1338538	journal	November 2013
Asymmetric Conjugate Addition of Alkynylboronates to Enones Chong, J. Michael; Shen, Lixin; Taylor, Nicholas J. Journal of the American Chemical Society, Vol. 122, Issue 8 https://doi.org/10.1021/ja992922b	journal	March 2000
Raising the p K _a Limit of “Soft” Nucleophiles in Palladium-Catalyzed Allylic Substitutions: Application of Diarylmethane Pronucleophiles Sha, Sheng-Chun; Zhang, Jiadi; Carroll, Patrick J. Journal of the American Chemical Society, Vol. 135, Issue 46 https://doi.org/10.1021/ja409511n	journal	November 2013
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
Unusual Allylpalladium Carboxylate Complexes: Identification of the Resting State of Catalytic Enantioselective Decarboxylative Allylic Alkylation Reactions of Ketones Sherden, Nathaniel H.; Behenna, Douglas C.; Virgil, Scott C. Angewandte Chemie International Edition, Vol. 48, Issue 37 https://doi.org/10.1002/anie.200902575	journal	September 2009
Origin of Selectivity of Tsuji-Trost Allylic Alkylation of Lactones: Highly Ordered Transition States with Lithium-Containing Enolates Patil, Mahendra; Thiel, Walter Chemistry - A European Journal, Vol. 18, Issue 33 https://doi.org/10.1002/chem.201201267	journal	June 2012
A DFT Study of the Effect of the Ligands in the Reductive Elimination from Palladium Bis(allyl) Complexes ^† Pérez-Rodríguez, Martín; Braga, Ataualpa A. C.; de Lera, Angel R. Organometallics, Vol. 29, Issue 21 https://doi.org/10.1021/om1001974	journal	November 2010
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
Recent Advances in Asymmetric Organocatalytic 1,4-Conjugate Additions Tsogoeva, Svetlana B. European Journal of Organic Chemistry, Vol. 2007, Issue 11 https://doi.org/10.1002/ejoc.200600653	journal	April 2007
A Pd(0)-Catalyzed Direct Dehydrative Coupling of Terminal Alkynes with Allylic Alcohols To Access 1,4-Enynes Li, Yang-Xiong; Xuan, Qing-Qing; Liu, Li Journal of the American Chemical Society, Vol. 135, Issue 34 https://doi.org/10.1021/ja406025p	journal	August 2013
Palladium-Catalyzed Decarboxylative Asymmetric Allylic Alkylation of Enol Carbonates Trost, Barry M.; Xu, Jiayi; Schmidt, Thomas Journal of the American Chemical Society, Vol. 131, Issue 51 https://doi.org/10.1021/ja9053948	journal	December 2009
Kinetic Resolution of Unsymmetrical Acyclic Allyl Carbonates Using Trimethylsilyl Cyanide via Palladium-Catalyzed Asymmetric Allylic Alkylation Bai, Da-Chang; Wang, Wan-Ying; Ding, Chang-Hua Synlett, Vol. 26, Issue 11 https://doi.org/10.1055/s-0034-1378709	journal	June 2015
The Art and Science of Total Synthesis at the Dawn of the Twenty-First Century Nicolaou, K. C.; Vourloumis, Dionisios; Winssinger, Nicolas Angewandte Chemie International Edition, Vol. 39, Issue 1 https://doi.org/10.1002/(SICI)1521-3773(20000103)39:1<44::AID-ANIE44>3.0.CO;2-L	journal	January 2000
Strategy for Employing Unstabilized Nucleophiles in Palladium-Catalyzed Asymmetric Allylic Alkylations Trost, Barry M.; Thaisrivongs, David A. Journal of the American Chemical Society, Vol. 130, Issue 43 https://doi.org/10.1021/ja806781u	journal	October 2008
Palladium-Catalyzed Allylic Cross-Coupling Reactions of Primary and Secondary Homoallylic Electrophiles Stokes, Benjamin J.; Opra, Susanne M.; Sigman, Matthew S. Journal of the American Chemical Society, Vol. 134, Issue 28 https://doi.org/10.1021/ja305403s	journal	July 2012
Enantioselective Construction of All-Carbon Quaternary Centers by Branch-Selective Pd-Catalyzed Allyl–Allyl Cross-Coupling Zhang, Ping; Le, Hai; Kyne, Robert E. Journal of the American Chemical Society, Vol. 133, Issue 25 https://doi.org/10.1021/ja2039248	journal	June 2011
Toward a More Complete Understanding of Noncovalent Interactions Involving Aromatic Rings Wheeler, Steven E.; Bloom, Jacob W. G. The Journal of Physical Chemistry A, Vol. 118, Issue 32 https://doi.org/10.1021/jp504415p	journal	July 2014
Steric Tuning of Silylacetylenes and Chiral Phosphine Ligands for Rhodium-Catalyzed Asymmetric Conjugate Alkynylation of Enones Nishimura, Takahiro; Guo, Xun-Xiang; Uchiyama, Nanase Journal of the American Chemical Society, Vol. 130, Issue 5 https://doi.org/10.1021/ja710540s	journal	February 2008
Rhodium-Catalyzed Asymmetric 1,4-Addition and Its Related Asymmetric Reactions Hayashi, Tamio; Yamasaki, Kaori Chemical Reviews, Vol. 103, Issue 8 https://doi.org/10.1021/cr020022z	journal	August 2003
Intramolecular Coupling of Allyl Carboxylates with Allyl Stannanes and Allyl Silanes: A New Type of Reductive Elimination Reaction? Méndez, María; Cuerva, Juan M.; Gómez-Bengoa, Enrique Chemistry - A European Journal, Vol. 8, Issue 16 https://doi.org/10.1002/1521-3765(20020816)8:16<3620::AID-CHEM3620>3.0.CO;2-P	journal	August 2002
Transition Metal-Catalyzed Asymmetric Allylation Ding, Chang-Hua; Hou, Xue-Long Asymmetric Catalysis from a Chinese Perspective https://doi.org/10.1007/978-3-642-19472-6_8	book	January 2011
Understanding Substituent Effects in Noncovalent Interactions Involving Aromatic Rings Wheeler, Steven E. Accounts of Chemical Research, Vol. 46, Issue 4 https://doi.org/10.1021/ar300109n	journal	June 2012
Enyne versus Diene RCM in the Synthesis of Cyclopentene Derivatives toward the A Ring of FR182877 Funel, Jacques-Alexis; Prunet, Joëlle The Journal of Organic Chemistry, Vol. 69, Issue 13 https://doi.org/10.1021/jo049557d	journal	June 2004
Catalytic Asymmetric Reduction of Allylic Esters with Formic Acid Catalyzed by Palladium-MOP Complexes Hayashi, Tamio; Iwamura, Hiroshi; Naito, Masaki Journal of the American Chemical Society, Vol. 116, Issue 2 https://doi.org/10.1021/ja00081a051	journal	January 1994
The Fate of Bis(η3-allyl)palladium Complexes in the Presence of Aldehydes (or Imines) and Allylic Chlorides: Stille Coupling versus Allylation of Aldehydes (or Imines) Nakamura, Hiroyuki; Bao, Ming; Yamamoto, Yoshinori Angewandte Chemie International Edition, Vol. 40, Issue 17 https://doi.org/10.1002/1521-3773(20010903)40:17<3208::AID-ANIE3208>3.0.CO;2-U	journal	September 2001
The total synthesis of (-)-cyanthiwigin F by means of double catalytic enantioselective alkylation Enquist Jr, John A.; Stoltz, Brian M. Nature, Vol. 453, Issue 7199 https://doi.org/10.1038/nature07046	journal	June 2008
Construction of 1,5-Enynes by Stereospecific Pd-Catalyzed Allyl–Propargyl Cross-Couplings Ardolino, Michael J.; Morken, James P. Journal of the American Chemical Society, Vol. 134, Issue 21 https://doi.org/10.1021/ja302329f	journal	May 2012
Stereoselective synthesis of aminocyclitol moieties of trehazolin and trehalostatin via enyne metathesis protocol Krishna, Palakodety Radha; Alivelu, Munagala Tetrahedron Letters, Vol. 51, Issue 48 https://doi.org/10.1016/j.tetlet.2010.09.084	journal	December 2010
Mechanistic aspects of C–C bond formation involving allylpalladium complexes: the role of computational studies Cárdenas, Diego J.; Echavarren, Antonio M. New J. Chem., Vol. 28, Issue 3 https://doi.org/10.1039/B315015A	journal	January 2004
Asymmetric Transition-Metal-Catalyzed Allylic Alkylations: Applications in Total Synthesis Trost, Barry M.; Crawley, Matthew L. Chemical Reviews, Vol. 103, Issue 8 https://doi.org/10.1021/cr020027w	journal	August 2003
Highly Enantioselective Michael Addition of Nitroalkanes to Enones and Its Application in Syntheses of (R)-Baclofen and (R)-Phenibut Guo, Xing-Tao; Shen, Jie; Sha, Feng Synthesis, Vol. 47, Issue 14 https://doi.org/10.1055/s-0034-1380203	journal	May 2015
Diastereocontrol in Asymmetric Allyl–Allyl Cross-Coupling: Stereocontrolled Reaction of Prochiral Allylboronates with Prochiral Allyl Chlorides Brozek, Laura A.; Ardolino, Michael J.; Morken, James P. Journal of the American Chemical Society, Vol. 133, Issue 42 https://doi.org/10.1021/ja2075967	journal	October 2011
Synthesis and determination of absolute configuration of tetracetate 4a-carba-d-xylofuranoside Xue, Zhi Jie; Chen, Ping; Peng, Shu Ying Tetrahedron, Vol. 62, Issue 1 https://doi.org/10.1016/j.tet.2005.09.139	journal	January 2006
Trifluoroacetic anhydride—catalyzed conjugate addition of boronic acids to α,β-unsaturated ketones Roscales, Silvia; Rincón, Ángela; Buxaderas, Eduardo Tetrahedron Letters, Vol. 53, Issue 35 https://doi.org/10.1016/j.tetlet.2012.06.105	journal	August 2012
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
The Pauson–Khand reaction, a powerful synthetic tool for the synthesis of complex molecules Blanco-Urgoiti, Jaime; Añorbe, Loreto; Pérez-Serrano, Leticia Chem. Soc. Rev., Vol. 33, Issue 1 https://doi.org/10.1039/B300976A	journal	January 2004
Synthesis of amino acid derivatives via enantio- and diastereoselective Pd-catalyzed allylic substitutions with a non-stabilized enolate as nucleophileThis work is dedicated to Professor Walter Siebert on the occasion of his 65th birthday. Weiß, Thomas D.; Helmchen, Günter; Kazmaier, Uli Chemical Communications, Issue 12 https://doi.org/10.1039/b203791m	journal	May 2002
Stereocomplementary Construction of Optically Active Bicyclo[4.3.0]nonenone Derivatives Mukai, Chisato; Kim, Jin Sung; Sonobe, Hiroshi The Journal of Organic Chemistry, Vol. 64, Issue 18 https://doi.org/10.1021/jo990819z	journal	September 1999
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
Recent Advances in Catalytic Enantioselective Michael Additions Krause, Norbert; Hoffmann-Röder, Anja Synthesis, Vol. 2001, Issue 02 https://doi.org/10.1055/s-2001-10803	journal	January 2001
The Inner-Sphere Process in the Enantioselective Tsuji Allylation Reaction with ( S )- t -Bu-phosphinooxazoline Ligands Keith, John A.; Behenna, Douglas C.; Mohr, Justin T. Journal of the American Chemical Society, Vol. 129, Issue 39 https://doi.org/10.1021/ja070516j	journal	October 2007
Enantioselectivity in Catalytic Asymmetric Fischer Indolizations Hinges on the Competition of π-Stacking and CH/π Interactions Seguin, Trevor J.; Lu, Tongxiang; Wheeler, Steven E. Organic Letters, Vol. 17, Issue 12 https://doi.org/10.1021/acs.orglett.5b01349	journal	June 2015
Metal-Catalyzed Enantioselective Allylation in Asymmetric Synthesis Lu, Zhan; Ma, Shengming Angewandte Chemie International Edition, Vol. 47, Issue 2 https://doi.org/10.1002/anie.200605113	journal	January 2008
Direct, Chemoselective N - tert -Prenylation of Indoles by CH Functionalization Luzung, Michael R.; Lewis, Chad A.; Baran, Phil S. Angewandte Chemie International Edition, Vol. 48, Issue 38 https://doi.org/10.1002/anie.200902761	journal	September 2009
Highly Enantioselective Palladium-Catalyzed Alkylation of Acyclic Amides Zhang, Kai; Peng, Qian; Hou, Xue-Long Angewandte Chemie International Edition, Vol. 47, Issue 9 https://doi.org/10.1002/anie.200704629	journal	February 2008
Stereochemistry of nucleophilic attack on π-allylpalladium complexes. Evidence for cis-migration of acetate from palladium to carbon Bäckvall, Jan-E.; Nordberg, Ruth E.; Björkman, Eva E. J. Chem. Soc., Chem. Commun., Issue 20 https://doi.org/10.1039/C39800000943	journal	January 1980
Synthesis of Carbohydrate-Derived Enynes and Subsequent Metathesis to Yield Polyhydroxylated 1-Vinylcycloalkenes Dolhem, Franck; Lièvre, Catherine; Demailly, Gilles European Journal of Organic Chemistry, Vol. 2003, Issue 12 https://doi.org/10.1002/ejoc.200300102	journal	June 2003
Highly Regio- and Enantioselective Pd-Catalyzed Allylic Alkylation and Amination of Monosubstituted Allylic Acetates with Novel Ferrocene P,N -Ligands You, Shu-Li; Zhu, Xia-Zhen; Luo, Yu-Mei Journal of the American Chemical Society, Vol. 123, Issue 30 https://doi.org/10.1021/ja016121w	journal	August 2001
Natural Products As Sources of New Drugs over the 30 Years from 1981 to 2010 Newman, David J.; Cragg, Gordon M. Journal of Natural Products, Vol. 75, Issue 3 https://doi.org/10.1021/np200906s	journal	January 2012
The Fate of Bis(η3-allyl)palladium Complexes in the Presence of Aldehydes (or Imines) and Allylic Chlorides: Stille Coupling versus Allylation of Aldehydes (or Imines) Nakamura, Hiroyuki; Bao, Ming; Yamamoto, Yoshinori Angewandte Chemie, Vol. 113, Issue 17 https://doi.org/10.1002/1521-3757(20010903)113:17<3308::aid-ange3308>3.0.co;2-q	journal	September 2001
Multinuclear Catalyst for Copper-Catalyzed Asymmetric Conjugate Addition of Organozinc Reagents Endo, Kohei; Ogawa, Mika; Shibata, Takanori Angewandte Chemie, Vol. 122, Issue 13 https://doi.org/10.1002/ange.200906839	journal	February 2010
Highly Enantioselective Palladium-Catalyzed Alkylation of Acyclic Amides Zhang, Kai; Peng, Qian; Hou, Xue-Long Angewandte Chemie, Vol. 120, Issue 9 https://doi.org/10.1002/ange.200704629	journal	February 2008
Unusual Allylpalladium Carboxylate Complexes: Identification of the Resting State of Catalytic Enantioselective Decarboxylative Allylic Alkylation Reactions of Ketones Sherden, Nathaniel H.; Behenna, Douglas C.; Virgil, Scott C. Angewandte Chemie, Vol. 121, Issue 37 https://doi.org/10.1002/ange.200902575	journal	September 2009
Synthesis of Carbohydrate-Derived Enynes and Subsequent Metathesis to Yield Polyhydroxylated 1-Vinylcycloalkenes. Dolhem, Franck; Lievre, Catherine; Demailly, Gilles ChemInform, Vol. 34, Issue 39 https://doi.org/10.1002/chin.200339190	journal	September 2003
Rhodium-Catalyzed Asymmetric 1,4-Addition and Its Related Asymmetric Reactions Hayashi, Tamio; Yamasaki, Kaori ChemInform, Vol. 34, Issue 44 https://doi.org/10.1002/chin.200344242	journal	November 2003
Asymmetric Transition-Metal-Catalyzed Allylic Alkylations: Applications in Total Synthesis Trost, Barry M.; Crawley, Matthew L. ChemInform, Vol. 34, Issue 44 https://doi.org/10.1002/chin.200344247	journal	November 2003
The Pauson—Khand Reaction, a Powerful Synthetic Tool for the Synthesis of Complex Molecules Blanco-Urgoiti, Jaime; Anorbe, Loreto; Perez-Serrano, Leticia ChemInform, Vol. 35, Issue 16 https://doi.org/10.1002/chin.200416259	journal	April 2004
Enyne Metathesis (Enyne Bond Reorganization) Diver, Steven T.; Giessert, Anthony J. ChemInform, Vol. 35, Issue 24 https://doi.org/10.1002/chin.200424248	journal	June 2004
Recent Advances in Asymmetric Organocatalytic 1,4-Conjugate Additions Tsogoeva, Svetlana B. ChemInform, Vol. 38, Issue 27 https://doi.org/10.1002/chin.200727221	journal	July 2007
N-Heterocyclic Carbenes Arduengo, Anthony J. Australian Journal of Chemistry, Vol. 64, Issue 8 https://doi.org/10.1071/ch11249	journal	January 2011
Handbook of organopalladium chemistry for organic synthesis Choice Reviews Online, Vol. 40, Issue 10, p. 40-5817-40-5817 https://doi.org/10.5860/choice.40-5817	journal	June 2003
Direct, Chemoselective N - tert -Prenylation of Indoles by CH Functionalization Luzung, Michael R.; Lewis, Chad A.; Baran, Phil S. Angewandte Chemie, Vol. 121, Issue 38 https://doi.org/10.1002/ange.200902761	journal	September 2009
Enyne versus Diene RCM in the Synthesis of Cyclopentene Derivatives toward the A Ring of FR182877. Funel, Jacques-Alexis; Prunet, Joëlle The Journal of Organic Chemistry, Vol. 69, Issue 16 https://doi.org/10.1021/jo048927v	journal	July 2004
Handbook of Organopalladium Chemistry for Organic Synthesis Harrowven, David C. Synthesis, Vol. 2003, Issue 04 https://doi.org/10.1055/s-2003-37640	journal	January 2003
Catalytic use of chiral phosphine ligands in asymmetric Pauson–Khand reactions Hiroi, Kunio; Watanabe, Takashi; Kawagishi, Ryoko Tetrahedron: Asymmetry, Vol. 11, Issue 3 https://doi.org/10.1016/s0957-4166(99)00570-4	journal	February 2000

Cited By (11)

Methanol as a Hydrogen Source in the Pd ^II −Bis( N -Heterocyclic Carbene)-Mediated Catalytic Semireduction of Alkynes Under Mild Reaction Conditions Prabusankar, Ganesan; Sathyanarayana, Arruri; Raju, Gembali Asian Journal of Organic Chemistry, Vol. 6, Issue 10 https://doi.org/10.1002/ajoc.201700326	journal	July 2017
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
Palladium-Catalyzed Asymmetric Construction of Vicinal Tertiary and All-Carbon Quaternary Stereocenters by Allylation of β-Ketocarbonyls with Morita-Baylis-Hillman Adducts Liu, Jiawang; Han, Zhaobin; Wang, Xiaoming Angewandte Chemie International Edition, Vol. 56, Issue 18 https://doi.org/10.1002/anie.201701455	journal	April 2017
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
Nucleophile Coordination Enabled Regioselectivity in Palladium-Catalyzed Asymmetric Allylic C−H Alkylation Fan, Lian-Feng; Luo, Shi-Wei; Chen, Shu-Sen Angewandte Chemie International Edition, Vol. 58, Issue 47 https://doi.org/10.1002/anie.201908960	journal	October 2019
Catalytic activity and facile recovery of a cyclometalated N‐heterocyclic carbene palladium(II) complex immobilized by non‐covalent interactions on reduced graphene oxide Karami, Kazem; Ramezanpour, Azar; Zakariazadeh, Mostafa Applied Organometallic Chemistry, Vol. 33, Issue 6 https://doi.org/10.1002/aoc.4907	journal	March 2019
Cationic [(Iminophosphine)Nickel(Allyl)] ⁺ Complexes as the First Example of Nickel Catalysts for Direct Hydroamination of Allenes Tafazolian, Hosein; Schmidt, Joseph A. R. Chemistry - A European Journal, Vol. 23, Issue 7 https://doi.org/10.1002/chem.201605611	journal	January 2017
Photocatalytic enantioselective α-aminoalkylation of acyclic imine derivatives by a chiral copper catalyst Han, Bowen; Li, Yanjun; Yu, Ying Nature Communications, Vol. 10, Issue 1 https://doi.org/10.1038/s41467-019-11688-7	journal	August 2019
A catalytic asymmetric construction of a tetrahydroquinoline-based spirooxindole framework via a diastereo- and enantioselective decarboxylative [4+2] cycloaddition Mei, Guang-Jian; Li, Dan; Zhou, Gui-Xiang Chemical Communications, Vol. 53, Issue 72 https://doi.org/10.1039/c7cc05595a	journal	January 2017
Pd-catalyzed enantioselective cyclopropanation of nitriles with mono substituted allyl carbonates enabled by the bulky N-heterocyclic carbene ligand Zhang, Gao-Peng; Huang, Shuai; Jiang, Yang-Jie Chemical Communications, Vol. 55, Issue 45 https://doi.org/10.1039/c9cc01960j	journal	January 2019
Nucleophile Coordination Enabled Regioselectivity in Palladium‐Catalyzed Asymmetric Allylic C−H Alkylation Fan, Lian‐Feng; Luo, Shi‐Wei; Chen, Shu‐Sen Angewandte Chemie, Vol. 131, Issue 47 https://doi.org/10.1002/ange.201908960	journal	November 2019

Linked Research (4)

Similar Records

Diastereo- and Enantioselective Iridium-Catalyzed Allylation of Cyclic Ketone Enolates: Synergetic Effect of Ligands and Barium Enolates

Journal Article · Thu Oct 30 00:00:00 EDT 2014 · Journal of the American Chemical Society · OSTI ID:1287338

Chen, Wenyong; Chen, Ming; Hartwig, John F.

Transition metal catalysis under high pressure: A useful liaison?!

Conference · Sun Dec 31 00:00:00 EST 1995 · OSTI ID:1287338

Hillers, S; Reiser, O

Synthesis and structural characterization of [eta superscript 3]-allyl([alpha]-diimine)nickel(II) complexes bearing trimethylsilyl groups

Journal Article · Fri Feb 10 00:00:00 EST 2012 · Journal of Organometallic Chemistry · OSTI ID:1287338

Ionkin, Alex S; Marshall, William J

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
asymmetric conjugate addition
chiral phosphine-ligands
c bond formation
allylpalladium complexes
reductive elimination
alpha-allylation
alkylation
construction
derivatives
metathesis

CCDC 1457162: Experimental Crystal Structure Determination: ARIBOU : 2-isopropyl-3-(2-methylphenyl)-1-phenylpent-4-en-1-one Bai, Da-Chang; Yu, Fei-Le; Wang, Wan-Ying https://doi.org/10.5517/ccdc.csd.cc1kx970 The current record is supplemented by this dataset	dataset	March 2016
CCDC 1457163: Experimental Crystal Structure Determination: ARIBUA : 1,3-diphenyl-2-(1-phenylethyl)pent-4-en-1-one Bai, Da-Chang; Yu, Fei-Le; Wang, Wan-Ying https://doi.org/10.5517/ccdc.csd.cc1kx981 The current record is supplemented by this dataset	dataset	March 2016
CCDC 1457165: Experimental Crystal Structure Determination: ARICAH : 3-methoxy-16-(1-phenylprop-2-en-1-yl)estra-1,3,5(10)-trien-17-one Bai, Da-Chang; Yu, Fei-Le; Wang, Wan-Ying https://doi.org/10.5517/ccdc.csd.cc1kx9b3 The current record is supplemented by this dataset	dataset	March 2016
CCDC 1457166: Experimental Crystal Structure Determination: ARICEL : 5-benzoyl-3-butyl-4-methyl-6-phenyl-4,5,6,6a-tetrahydropentalen-2(1H)-one Bai, Da-Chang; Yu, Fei-Le; Wang, Wan-Ying https://doi.org/10.5517/ccdc.csd.cc1kx9c4 The current record is supplemented by this dataset	dataset	March 2016