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Chiral Counteranions in Asymmetric Transition-Metal Catalysis: Highly Enantioselective Pd/Brønsted Acid-Catalyzed Direct α-Allylation of Aldehydes
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Section:Abstract
We have developed a highly enantioselective Pd/chiral acid-catalyzed α-allylation of α-branched aldehydes with an allyl amine as the allylating species that creates all-carbon quaternary stereogenic centers in high yields and enantioselectivities. To our knowledge, this is the first time that a chiral anionic ligand is applied for achieving asymmetric induction in a palladium-catalyzed allylic alkylation reaction.
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This article has been cited by 42 ACS Journal articles (5 most recent appear below).
Enantio- and Diastereoselective Organocatalytic α-Alkylation of Aldehydes with 3-Substituted 2-(Bromomethyl)acrylates
Jacqueline Jiménez, Aitor Landa, Aitziber Lizarraga, Miguel Maestro, Antonia Mielgo, Mikel Oiarbide, Irene Velilla, and Claudio PalomoThe Journal of Organic Chemistry2012 77 (1), 747-753Enantio- and Diastereoselective Organocatalytic α-Alkylation of Aldehydes with 3-Substituted 2-(Bromomethyl)acrylates
Jacqueline Jiménez, Aitor Landa, Aitziber Lizarraga, Miguel Maestro, Antonia Mielgo, Mikel Oiarbide, Irene Velilla, and Claudio PalomoThe Journal of Organic Chemistry2012 77 (1), 747-753The catalytic direct α-alkylation of aldehydes with 2-(bromomethyl)acrylates has been accomplished, giving rise to α-branched and functionalized aldehydes of high diastereo- and enantiopurity. The influence of the nature of the ester group of the ...
C–N Bond Cleavage of Allylic Amines via Hydrogen Bond Activation with Alcohol Solvents in Pd-Catalyzed Allylic Alkylation of Carbonyl Compounds
Xiaohu Zhao, Delong Liu, Hui Guo, Yangang Liu, and Wanbin ZhangJournal of the American Chemical Society2011 133 (48), 19354-19357C–N Bond Cleavage of Allylic Amines via Hydrogen Bond Activation with Alcohol Solvents in Pd-Catalyzed Allylic Alkylation of Carbonyl Compounds
Xiaohu Zhao, Delong Liu, Hui Guo, Yangang Liu, and Wanbin ZhangJournal of the American Chemical Society2011 133 (48), 19354-19357Hydrogen-bond-activated C–N bond cleavage of allylic amines was realized in Pd-catalyzed allylic alkylation to form the C–C bond product. The method could be expanded to a series of allylic amines and carbonyl compounds with excellent results. It provides ...
Cooperative Thiourea–Brønsted Acid Organocatalysis: Enantioselective Cyanosilylation of Aldehydes with TMSCN
Zhiguo Zhang, Katharina M. Lippert, Heike Hausmann, Mike Kotke, and Peter R. SchreinerThe Journal of Organic Chemistry2011 76 (23), 9764-9776Cooperative Thiourea–Brønsted Acid Organocatalysis: Enantioselective Cyanosilylation of Aldehydes with TMSCN
Zhiguo Zhang, Katharina M. Lippert, Heike Hausmann, Mike Kotke, and Peter R. SchreinerThe Journal of Organic Chemistry2011 76 (23), 9764-9776We report a new thiourea–Brønsted acid cooperative catalytic system for the enantioselective cyanosilylation of aldehydes with yields up to 90% and enantioselectivities up to 88%. The addition of an achiral acid was found to be crucial for high asymmetric ...
Diastereoselective Control of Intramolecular Aza-Michael Reactions Using Achiral Catalysts
Cheng Zhong, Yikai Wang, Alvin W. Hung, Stuart L. Schreiber, and Damian W. YoungOrganic Letters2011 13 (20), 5556-5559Diastereoselective Control of Intramolecular Aza-Michael Reactions Using Achiral Catalysts
Cheng Zhong, Yikai Wang, Alvin W. Hung, Stuart L. Schreiber, and Damian W. YoungOrganic Letters2011 13 (20), 5556-5559An intramolecular aza-Michael reaction with a Cbz carbamate and an enone is reported to result in 3,5-disubstituted nitrogen-containing heterocycles. Either cis or trans isomers were obtained selectively using chiral substrates and an achiral Pd (II) ...
Catalytic Enantioselective Desymmetrization of meso-Diamines: A Dual Small-Molecule Catalysis Approach
Chandra Kanta De and Daniel SeidelJournal of the American Chemical Society2011 133 (37), 14538-14541Catalytic Enantioselective Desymmetrization of meso-Diamines: A Dual Small-Molecule Catalysis Approach
Chandra Kanta De and Daniel SeidelJournal of the American Chemical Society2011 133 (37), 14538-14541The desymmetrization of meso-diamines was accomplished via enantioselective monobenzoylation facilitated by the cooperative action of two small-molecule catalysts. A chiral acyl-transfer reagent is formed in situ through the interplay of benzoic anhydride,...
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History
- Published In Issue September 19, 2007
- Received June 26, 2007
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