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

Abstract

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.

Authors:
 [1];  [1];  [1];  [1];  [1];  [1];  [1]; ORCiD logo [2]; ORCiD logo [3]
+ Show Author Affiliations
  1. Chinese Academy of Sciences, Shanghai (China). State Key Laboratory of Organometallic Chemistry, Shanghai Instit. of Organic Chemistry
  2. Cornell University, Ithaca, NY (United States). Dept. of Chemistry and Chemical Biology, Baker Laboratory
  3. 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
Publication Date:
Research Org.:
Chinese Academy of Sciences, Shanghai (China); Energy Frontier Research Centers (EFRC) (United States). Energy Frontier Research in Extreme Environments (EFree)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES)
OSTI Identifier:
1287338
Grant/Contract Number:  
SC0001057
Resource Type:
Accepted Manuscript
Journal Name:
Nature Communications
Additional Journal Information:
Journal Volume: 7; Journal ID: ISSN 2041-1723
Publisher:
Nature Publishing Group
Country of Publication:
United States
Language:
English
Subject:
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

Citation Formats

Bai, Da -Chang, Yu, Fei -Le, Wang, Wan -Ying, Chen, Di, Li, Hao, Liu, Qing -Rong, Ding, Chang -Hua, Chen, Bo, and Hou, Xue -Long. Palladium/N-heterocyclic carbene catalysed regio and diastereoselective reaction of ketones with allyl reagents via inner-sphere mechanism. United States: N. p., 2016. Web. doi:10.1038/ncomms11806.
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Bai, Da -Chang, Yu, Fei -Le, Wang, Wan -Ying, Chen, Di, Li, Hao, Liu, Qing -Rong, Ding, Chang -Hua, Chen, Bo, & Hou, Xue -Long. Palladium/N-heterocyclic carbene catalysed regio and diastereoselective reaction of ketones with allyl reagents via inner-sphere mechanism. United States. https://doi.org/10.1038/ncomms11806
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Bai, Da -Chang, Yu, Fei -Le, Wang, Wan -Ying, Chen, Di, Li, Hao, Liu, Qing -Rong, Ding, Chang -Hua, Chen, Bo, and Hou, Xue -Long. Fri . "Palladium/N-heterocyclic carbene catalysed regio and diastereoselective reaction of ketones with allyl reagents via inner-sphere mechanism". United States. https://doi.org/10.1038/ncomms11806. https://www.osti.gov/servlets/purl/1287338.
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@article{osti_1287338,
title = {Palladium/N-heterocyclic carbene catalysed regio and diastereoselective reaction of ketones with allyl reagents via inner-sphere mechanism},
author = {Bai, Da -Chang and Yu, Fei -Le and Wang, Wan -Ying and Chen, Di and Li, Hao and Liu, Qing -Rong and Ding, Chang -Hua and Chen, Bo and Hou, Xue -Long},
abstractNote = {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.},
doi = {10.1038/ncomms11806},
journal = {Nature Communications},
number = ,
volume = 7,
place = {United States},
year = {Fri Jun 10 00:00:00 EDT 2016},
month = {Fri Jun 10 00:00:00 EDT 2016}
}
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https://doi.org/10.1038/ncomms11806
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Works referenced in this record:

Multinuclear Catalyst for Copper-Catalyzed Asymmetric Conjugate Addition of Organozinc Reagents
journal, February 2010

  • Endo, Kohei; Ogawa, Mika; Shibata, Takanori
  • Angewandte Chemie International Edition, Vol. 49, Issue 13
  • DOI: 10.1002/anie.200906839

Congested C–C Bonds by Pd-Catalyzed Enantioselective Allyl–Allyl Cross-Coupling, a Mechanism-Guided Solution
journal, April 2014

  • Ardolino, Michael J.; Morken, James P.
  • Journal of the American Chemical Society, Vol. 136, Issue 19
  • DOI: 10.1021/ja502280w

Aiming for the Ideal Synthesis
journal, July 2010

  • Gaich, Tanja; Baran, Phil S.
  • The Journal of Organic Chemistry, Vol. 75, Issue 14
  • DOI: 10.1021/jo1006812

Graphene-Based Photocatalysts for Solar-Fuel Generation
journal, June 2015

  • Xiang, Quanjun; Cheng, Bei; Yu, Jiaguo
  • Angewandte Chemie International Edition, Vol. 54, Issue 39
  • DOI: 10.1002/anie.201411096

Enyne Metathesis (Enyne Bond Reorganization)
journal, March 2004

  • Diver, Steven T.; Giessert, Anthony J.
  • Chemical Reviews, Vol. 104, Issue 3
  • DOI: 10.1021/cr020009e

Pd-Catalyzed Enantioselective Allyl−Allyl Cross-Coupling
journal, August 2010

  • Zhang, Ping; Brozek, Laura A.; Morken, James P.
  • Journal of the American Chemical Society, Vol. 132, Issue 31
  • DOI: 10.1021/ja105161f

Asymmetric Conjugate Addition of Alkynylboronates to Enones
journal, March 2000

  • Chong, J. Michael; Shen, Lixin; Taylor, Nicholas J.
  • Journal of the American Chemical Society, Vol. 122, Issue 8
  • DOI: 10.1021/ja992922b

Raising the p K a Limit of “Soft” Nucleophiles in Palladium-Catalyzed Allylic Substitutions: Application of Diarylmethane Pronucleophiles
journal, November 2013

  • Sha, Sheng-Chun; Zhang, Jiadi; Carroll, Patrick J.
  • Journal of the American Chemical Society, Vol. 135, Issue 46
  • DOI: 10.1021/ja409511n

Chiral Counteranions in Asymmetric Transition-Metal Catalysis:  Highly Enantioselective Pd/Brønsted Acid-Catalyzed Direct α-Allylation of Aldehydes
journal, September 2007

  • Mukherjee, Santanu; List, Benjamin
  • Journal of the American Chemical Society, Vol. 129, Issue 37
  • DOI: 10.1021/ja074678r

Unusual Allylpalladium Carboxylate Complexes: Identification of the Resting State of Catalytic Enantioselective Decarboxylative Allylic Alkylation Reactions of Ketones
journal, September 2009

  • Sherden, Nathaniel H.; Behenna, Douglas C.; Virgil, Scott C.
  • Angewandte Chemie International Edition, Vol. 48, Issue 37
  • DOI: 10.1002/anie.200902575

Origin of Selectivity of Tsuji-Trost Allylic Alkylation of Lactones: Highly Ordered Transition States with Lithium-Containing Enolates
journal, June 2012

  • Patil, Mahendra; Thiel, Walter
  • Chemistry - A European Journal, Vol. 18, Issue 33
  • DOI: 10.1002/chem.201201267

A DFT Study of the Effect of the Ligands in the Reductive Elimination from Palladium Bis(allyl) Complexes †
journal, November 2010

  • Pérez-Rodríguez, Martín; Braga, Ataualpa A. C.; de Lera, Angel R.
  • Organometallics, Vol. 29, Issue 21
  • DOI: 10.1021/om1001974

The Reaction Mechanism of the Enantioselective Tsuji Allylation: Inner-Sphere and Outer-Sphere Pathways, Internal Rearrangements, and Asymmetric C–C Bond Formation
journal, November 2012

  • Keith, John A.; Behenna, Douglas C.; Sherden, Nathaniel
  • Journal of the American Chemical Society, Vol. 134, Issue 46
  • DOI: 10.1021/ja306860n

Recent Advances in Asymmetric Organocatalytic 1,4-Conjugate Additions
journal, April 2007

  • Tsogoeva, Svetlana B.
  • European Journal of Organic Chemistry, Vol. 2007, Issue 11
  • DOI: 10.1002/ejoc.200600653

A Pd(0)-Catalyzed Direct Dehydrative Coupling of Terminal Alkynes with Allylic Alcohols To Access 1,4-Enynes
journal, August 2013

  • Li, Yang-Xiong; Xuan, Qing-Qing; Liu, Li
  • Journal of the American Chemical Society, Vol. 135, Issue 34
  • DOI: 10.1021/ja406025p

Palladium-Catalyzed Decarboxylative Asymmetric Allylic Alkylation of Enol Carbonates
journal, December 2009

  • Trost, Barry M.; Xu, Jiayi; Schmidt, Thomas
  • Journal of the American Chemical Society, Vol. 131, Issue 51
  • DOI: 10.1021/ja9053948

The Art and Science of Total Synthesis at the Dawn of the Twenty-First Century
journal, January 2000

Strategy for Employing Unstabilized Nucleophiles in Palladium-Catalyzed Asymmetric Allylic Alkylations
journal, October 2008

  • Trost, Barry M.; Thaisrivongs, David A.
  • Journal of the American Chemical Society, Vol. 130, Issue 43
  • DOI: 10.1021/ja806781u

Palladium-Catalyzed Allylic Cross-Coupling Reactions of Primary and Secondary Homoallylic Electrophiles
journal, July 2012

  • Stokes, Benjamin J.; Opra, Susanne M.; Sigman, Matthew S.
  • Journal of the American Chemical Society, Vol. 134, Issue 28
  • DOI: 10.1021/ja305403s

Enantioselective Construction of All-Carbon Quaternary Centers by Branch-Selective Pd-Catalyzed Allyl–Allyl Cross-Coupling
journal, June 2011

  • Zhang, Ping; Le, Hai; Kyne, Robert E.
  • Journal of the American Chemical Society, Vol. 133, Issue 25
  • DOI: 10.1021/ja2039248

Toward a More Complete Understanding of Noncovalent Interactions Involving Aromatic Rings
journal, July 2014

  • Wheeler, Steven E.; Bloom, Jacob W. G.
  • The Journal of Physical Chemistry A, Vol. 118, Issue 32
  • DOI: 10.1021/jp504415p

Steric Tuning of Silylacetylenes and Chiral Phosphine Ligands for Rhodium-Catalyzed Asymmetric Conjugate Alkynylation of Enones
journal, February 2008

  • Nishimura, Takahiro; Guo, Xun-Xiang; Uchiyama, Nanase
  • Journal of the American Chemical Society, Vol. 130, Issue 5
  • DOI: 10.1021/ja710540s

Rhodium-Catalyzed Asymmetric 1,4-Addition and Its Related Asymmetric Reactions
journal, August 2003

  • Hayashi, Tamio; Yamasaki, Kaori
  • Chemical Reviews, Vol. 103, Issue 8
  • DOI: 10.1021/cr020022z

Intramolecular Coupling of Allyl Carboxylates with Allyl Stannanes and Allyl Silanes: A New Type of Reductive Elimination Reaction?
journal, August 2002

Transition Metal-Catalyzed Asymmetric Allylation
book, January 2011

Understanding Substituent Effects in Noncovalent Interactions Involving Aromatic Rings
journal, June 2012

  • Wheeler, Steven E.
  • Accounts of Chemical Research, Vol. 46, Issue 4
  • DOI: 10.1021/ar300109n

Enyne versus Diene RCM in the Synthesis of Cyclopentene Derivatives toward the A Ring of FR182877
journal, June 2004

  • Funel, Jacques-Alexis; Prunet, Joëlle
  • The Journal of Organic Chemistry, Vol. 69, Issue 13
  • DOI: 10.1021/jo049557d

Catalytic Asymmetric Reduction of Allylic Esters with Formic Acid Catalyzed by Palladium-MOP Complexes
journal, January 1994

  • Hayashi, Tamio; Iwamura, Hiroshi; Naito, Masaki
  • Journal of the American Chemical Society, Vol. 116, Issue 2
  • DOI: 10.1021/ja00081a051

The total synthesis of (-)-cyanthiwigin F by means of double catalytic enantioselective alkylation
journal, June 2008

Construction of 1,5-Enynes by Stereospecific Pd-Catalyzed Allyl–Propargyl Cross-Couplings
journal, May 2012

  • Ardolino, Michael J.; Morken, James P.
  • Journal of the American Chemical Society, Vol. 134, Issue 21
  • DOI: 10.1021/ja302329f

Stereoselective synthesis of aminocyclitol moieties of trehazolin and trehalostatin via enyne metathesis protocol
journal, December 2010

Mechanistic aspects of C–C bond formation involving allylpalladium complexes: the role of computational studies
journal, January 2004

  • Cárdenas, Diego J.; Echavarren, Antonio M.
  • New J. Chem., Vol. 28, Issue 3
  • DOI: 10.1039/B315015A

Asymmetric Transition-Metal-Catalyzed Allylic Alkylations:  Applications in Total Synthesis
journal, August 2003

  • Trost, Barry M.; Crawley, Matthew L.
  • Chemical Reviews, Vol. 103, Issue 8
  • DOI: 10.1021/cr020027w

Diastereocontrol in Asymmetric Allyl–Allyl Cross-Coupling: Stereocontrolled Reaction of Prochiral Allylboronates with Prochiral Allyl Chlorides
journal, October 2011

  • Brozek, Laura A.; Ardolino, Michael J.; Morken, James P.
  • Journal of the American Chemical Society, Vol. 133, Issue 42
  • DOI: 10.1021/ja2075967

Synthesis and determination of absolute configuration of tetracetate 4a-carba-d-xylofuranoside
journal, January 2006

Trifluoroacetic anhydride—catalyzed conjugate addition of boronic acids to α,β-unsaturated ketones
journal, August 2012

Chemo- and Regioselectivity-Tunable Pd-Catalyzed Allylic Alkylation of Imines
journal, September 2011

  • Chen, Jian-Ping; Peng, Qian; Lei, Bai-Lin
  • Journal of the American Chemical Society, Vol. 133, Issue 36
  • DOI: 10.1021/ja2039503

The Pauson–Khand reaction, a powerful synthetic tool for the synthesis of complex molecules
journal, January 2004

  • Blanco-Urgoiti, Jaime; Añorbe, Loreto; Pérez-Serrano, Leticia
  • Chem. Soc. Rev., Vol. 33, Issue 1
  • DOI: 10.1039/B300976A

Stereocomplementary Construction of Optically Active Bicyclo[4.3.0]nonenone Derivatives
journal, September 1999

  • Mukai, Chisato; Kim, Jin Sung; Sonobe, Hiroshi
  • The Journal of Organic Chemistry, Vol. 64, Issue 18
  • DOI: 10.1021/jo990819z

Direct Asymmetric α-Allylation of Aldehydes with Simple Allylic Alcohols Enabled by the Concerted Action of Three Different Catalysts
journal, September 2011

  • Jiang, Gaoxi; List, Benjamin
  • Angewandte Chemie International Edition, Vol. 50, Issue 40
  • DOI: 10.1002/anie.201103263

Recent Advances in Catalytic Enantioselective Michael Additions
journal, January 2001

The Inner-Sphere Process in the Enantioselective Tsuji Allylation Reaction with ( S )- t -Bu-phosphinooxazoline Ligands
journal, October 2007

  • Keith, John A.; Behenna, Douglas C.; Mohr, Justin T.
  • Journal of the American Chemical Society, Vol. 129, Issue 39
  • DOI: 10.1021/ja070516j

Enantioselectivity in Catalytic Asymmetric Fischer Indolizations Hinges on the Competition of π-Stacking and CH/π Interactions
journal, June 2015

Metal-Catalyzed Enantioselective Allylation in Asymmetric Synthesis
journal, January 2008

  • Lu, Zhan; Ma, Shengming
  • Angewandte Chemie International Edition, Vol. 47, Issue 2
  • DOI: 10.1002/anie.200605113

Direct, Chemoselective N - tert -Prenylation of Indoles by CH Functionalization
journal, September 2009

  • Luzung, Michael R.; Lewis, Chad A.; Baran, Phil S.
  • Angewandte Chemie International Edition, Vol. 48, Issue 38
  • DOI: 10.1002/anie.200902761

Highly Enantioselective Palladium-Catalyzed Alkylation of Acyclic Amides
journal, February 2008

  • Zhang, Kai; Peng, Qian; Hou, Xue-Long
  • Angewandte Chemie International Edition, Vol. 47, Issue 9
  • DOI: 10.1002/anie.200704629

Stereochemistry of nucleophilic attack on π-allylpalladium complexes. Evidence for cis-migration of acetate from palladium to carbon
journal, January 1980

  • Bäckvall, Jan-E.; Nordberg, Ruth E.; Björkman, Eva E.
  • J. Chem. Soc., Chem. Commun., Issue 20
  • DOI: 10.1039/C39800000943

Synthesis of Carbohydrate-Derived Enynes and Subsequent Metathesis to Yield Polyhydroxylated 1-Vinylcycloalkenes
journal, June 2003

  • Dolhem, Franck; Lièvre, Catherine; Demailly, Gilles
  • European Journal of Organic Chemistry, Vol. 2003, Issue 12
  • DOI: 10.1002/ejoc.200300102

Highly Regio- and Enantioselective Pd-Catalyzed Allylic Alkylation and Amination of Monosubstituted Allylic Acetates with Novel Ferrocene P,N -Ligands
journal, August 2001

  • You, Shu-Li; Zhu, Xia-Zhen; Luo, Yu-Mei
  • Journal of the American Chemical Society, Vol. 123, Issue 30
  • DOI: 10.1021/ja016121w

Natural Products As Sources of New Drugs over the 30 Years from 1981 to 2010
journal, January 2012

  • Newman, David J.; Cragg, Gordon M.
  • Journal of Natural Products, Vol. 75, Issue 3
  • DOI: 10.1021/np200906s

Multinuclear Catalyst for Copper-Catalyzed Asymmetric Conjugate Addition of Organozinc Reagents
journal, February 2010

  • Endo, Kohei; Ogawa, Mika; Shibata, Takanori
  • Angewandte Chemie, Vol. 122, Issue 13
  • DOI: 10.1002/ange.200906839

Highly Enantioselective Palladium-Catalyzed Alkylation of Acyclic Amides
journal, February 2008

Unusual Allylpalladium Carboxylate Complexes: Identification of the Resting State of Catalytic Enantioselective Decarboxylative Allylic Alkylation Reactions of Ketones
journal, September 2009

  • Sherden, Nathaniel H.; Behenna, Douglas C.; Virgil, Scott C.
  • Angewandte Chemie, Vol. 121, Issue 37
  • DOI: 10.1002/ange.200902575

Synthesis of Carbohydrate-Derived Enynes and Subsequent Metathesis to Yield Polyhydroxylated 1-Vinylcycloalkenes.
journal, September 2003

  • Dolhem, Franck; Lievre, Catherine; Demailly, Gilles
  • ChemInform, Vol. 34, Issue 39
  • DOI: 10.1002/chin.200339190

Rhodium-Catalyzed Asymmetric 1,4-Addition and Its Related Asymmetric Reactions
journal, November 2003

Asymmetric Transition-Metal-Catalyzed Allylic Alkylations: Applications in Total Synthesis
journal, November 2003

The Pauson—Khand Reaction, a Powerful Synthetic Tool for the Synthesis of Complex Molecules
journal, April 2004

  • Blanco-Urgoiti, Jaime; Anorbe, Loreto; Perez-Serrano, Leticia
  • ChemInform, Vol. 35, Issue 16
  • DOI: 10.1002/chin.200416259

Enyne Metathesis (Enyne Bond Reorganization)
journal, June 2004

Recent Advances in Asymmetric Organocatalytic 1,4-Conjugate Additions
journal, July 2007

N-Heterocyclic Carbenes
journal, January 2011

  • Arduengo, Anthony J.
  • Australian Journal of Chemistry, Vol. 64, Issue 8
  • DOI: 10.1071/ch11249

Handbook of organopalladium chemistry for organic synthesis
journal, June 2003

Direct, Chemoselective N - tert -Prenylation of Indoles by CH Functionalization
journal, September 2009

  • Luzung, Michael R.; Lewis, Chad A.; Baran, Phil S.
  • Angewandte Chemie, Vol. 121, Issue 38
  • DOI: 10.1002/ange.200902761

Enyne versus Diene RCM in the Synthesis of Cyclopentene Derivatives toward the A Ring of FR182877.
journal, July 2004

  • Funel, Jacques-Alexis; Prunet, Joëlle
  • The Journal of Organic Chemistry, Vol. 69, Issue 16
  • DOI: 10.1021/jo048927v

Handbook of Organopalladium Chemistry for Organic Synthesis
journal, January 2003

Unusual Allylpalladium Carboxylate Complexes: Identification of the Resting State of Catalytic Enantioselective Decarboxylative Allylic Alkylation Reactions of Ketones
journal, September 2009

  • Sherden, Nathaniel H.; Behenna, Douglas C.; Virgil, Scott C.
  • Angewandte Chemie International Edition, Vol. 48, Issue 37
  • DOI: 10.1002/anie.200902575

Direct, Chemoselective N - tert -Prenylation of Indoles by CH Functionalization
journal, September 2009

  • Luzung, Michael R.; Lewis, Chad A.; Baran, Phil S.
  • Angewandte Chemie International Edition, Vol. 48, Issue 38
  • DOI: 10.1002/anie.200902761

Rhodium-Catalyzed Asymmetric 1,4-Addition and Its Related Asymmetric Reactions
journal, November 2003

Enyne Metathesis (Enyne Bond Reorganization)
journal, June 2004

Synthesis of Carbohydrate-Derived Enynes and Subsequent Metathesis to Yield Polyhydroxylated 1-Vinylcycloalkenes
journal, June 2003

  • Dolhem, Franck; Lièvre, Catherine; Demailly, Gilles
  • European Journal of Organic Chemistry, Vol. 2003, Issue 12
  • DOI: 10.1002/ejoc.200300102

Trifluoroacetic anhydride—catalyzed conjugate addition of boronic acids to α,β-unsaturated ketones
journal, August 2012

Catalytic use of chiral phosphine ligands in asymmetric Pauson–Khand reactions
journal, February 2000

Enantioselectivity in Catalytic Asymmetric Fischer Indolizations Hinges on the Competition of π-Stacking and CH/π Interactions
journal, June 2015

Understanding Substituent Effects in Noncovalent Interactions Involving Aromatic Rings
journal, June 2012

  • Wheeler, Steven E.
  • Accounts of Chemical Research, Vol. 46, Issue 4
  • DOI: 10.1021/ar300109n

The Inner-Sphere Process in the Enantioselective Tsuji Allylation Reaction with ( S )- t -Bu-phosphinooxazoline Ligands
journal, October 2007

  • Keith, John A.; Behenna, Douglas C.; Mohr, Justin T.
  • Journal of the American Chemical Society, Vol. 129, Issue 39
  • DOI: 10.1021/ja070516j

Chiral Counteranions in Asymmetric Transition-Metal Catalysis:  Highly Enantioselective Pd/Brønsted Acid-Catalyzed Direct α-Allylation of Aldehydes
journal, September 2007

  • Mukherjee, Santanu; List, Benjamin
  • Journal of the American Chemical Society, Vol. 129, Issue 37
  • DOI: 10.1021/ja074678r

Enantioselective Construction of All-Carbon Quaternary Centers by Branch-Selective Pd-Catalyzed Allyl–Allyl Cross-Coupling
journal, June 2011

  • Zhang, Ping; Le, Hai; Kyne, Robert E.
  • Journal of the American Chemical Society, Vol. 133, Issue 25
  • DOI: 10.1021/ja2039248

Diastereocontrol in Asymmetric Allyl–Allyl Cross-Coupling: Stereocontrolled Reaction of Prochiral Allylboronates with Prochiral Allyl Chlorides
journal, October 2011

  • Brozek, Laura A.; Ardolino, Michael J.; Morken, James P.
  • Journal of the American Chemical Society, Vol. 133, Issue 42
  • DOI: 10.1021/ja2075967

Construction of 1,5-Enynes by Stereospecific Pd-Catalyzed Allyl–Propargyl Cross-Couplings
journal, May 2012

  • Ardolino, Michael J.; Morken, James P.
  • Journal of the American Chemical Society, Vol. 134, Issue 21
  • DOI: 10.1021/ja302329f

Palladium-Catalyzed Allylic Cross-Coupling Reactions of Primary and Secondary Homoallylic Electrophiles
journal, July 2012

  • Stokes, Benjamin J.; Opra, Susanne M.; Sigman, Matthew S.
  • Journal of the American Chemical Society, Vol. 134, Issue 28
  • DOI: 10.1021/ja305403s

The Reaction Mechanism of the Enantioselective Tsuji Allylation: Inner-Sphere and Outer-Sphere Pathways, Internal Rearrangements, and Asymmetric C–C Bond Formation
journal, November 2012

  • Keith, John A.; Behenna, Douglas C.; Sherden, Nathaniel
  • Journal of the American Chemical Society, Vol. 134, Issue 46
  • DOI: 10.1021/ja306860n

A Pd(0)-Catalyzed Direct Dehydrative Coupling of Terminal Alkynes with Allylic Alcohols To Access 1,4-Enynes
journal, August 2013

  • Li, Yang-Xiong; Xuan, Qing-Qing; Liu, Li
  • Journal of the American Chemical Society, Vol. 135, Issue 34
  • DOI: 10.1021/ja406025p

Raising the p K a Limit of “Soft” Nucleophiles in Palladium-Catalyzed Allylic Substitutions: Application of Diarylmethane Pronucleophiles
journal, November 2013

  • Sha, Sheng-Chun; Zhang, Jiadi; Carroll, Patrick J.
  • Journal of the American Chemical Society, Vol. 135, Issue 46
  • DOI: 10.1021/ja409511n

Congested C–C Bonds by Pd-Catalyzed Enantioselective Allyl–Allyl Cross-Coupling, a Mechanism-Guided Solution
journal, April 2014

  • Ardolino, Michael J.; Morken, James P.
  • Journal of the American Chemical Society, Vol. 136, Issue 19
  • DOI: 10.1021/ja502280w

Steric Tuning of Silylacetylenes and Chiral Phosphine Ligands for Rhodium-Catalyzed Asymmetric Conjugate Alkynylation of Enones
journal, February 2008

  • Nishimura, Takahiro; Guo, Xun-Xiang; Uchiyama, Nanase
  • Journal of the American Chemical Society, Vol. 130, Issue 5
  • DOI: 10.1021/ja710540s

Strategy for Employing Unstabilized Nucleophiles in Palladium-Catalyzed Asymmetric Allylic Alkylations
journal, October 2008

  • Trost, Barry M.; Thaisrivongs, David A.
  • Journal of the American Chemical Society, Vol. 130, Issue 43
  • DOI: 10.1021/ja806781u

Palladium-Catalyzed Decarboxylative Asymmetric Allylic Alkylation of Enol Carbonates
journal, December 2009

  • Trost, Barry M.; Xu, Jiayi; Schmidt, Thomas
  • Journal of the American Chemical Society, Vol. 131, Issue 51
  • DOI: 10.1021/ja9053948

Enyne versus Diene RCM in the Synthesis of Cyclopentene Derivatives toward the A Ring of FR182877.
journal, July 2004

  • Funel, Jacques-Alexis; Prunet, Joëlle
  • The Journal of Organic Chemistry, Vol. 69, Issue 16
  • DOI: 10.1021/jo048927v

Aiming for the Ideal Synthesis
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Stereocomplementary Construction of Optically Active Bicyclo[4.3.0]nonenone Derivatives
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  • Mukai, Chisato; Kim, Jin Sung; Sonobe, Hiroshi
  • The Journal of Organic Chemistry, Vol. 64, Issue 18
  • DOI: 10.1021/jo990819z

Toward a More Complete Understanding of Noncovalent Interactions Involving Aromatic Rings
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  • Wheeler, Steven E.; Bloom, Jacob W. G.
  • The Journal of Physical Chemistry A, Vol. 118, Issue 32
  • DOI: 10.1021/jp504415p

Natural Products As Sources of New Drugs over the 30 Years from 1981 to 2010
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  • Newman, David J.; Cragg, Gordon M.
  • Journal of Natural Products, Vol. 75, Issue 3
  • DOI: 10.1021/np200906s

The total synthesis of (-)-cyanthiwigin F by means of double catalytic enantioselective alkylation
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    Photocatalytic enantioselective α-aminoalkylation of acyclic imine derivatives by a chiral copper catalyst
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