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Catalytic Asymmetric Addition of Alcohols to Imines: Enantioselective Preparation of Chiral N,O-Aminals
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University of South Florida.
, ‡Louisiana State University.
Section:Abstract
The enantioselective addition of alcohols to imine electrophiles has been shown to proceed in the presence of a catalytic amount of a chiral phosphoric acid catalyst. The reaction allows for the formation of the respective chiral N,O-aminals in excellent yield and enantioselectivity. A total of 11 different alcohols and 11 different imines were successfully used as a clear demonstration of the reaction generality.
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This article has been cited by 20 ACS Journal articles (5 most recent appear below).
Chiral Phosphoric Acid-Catalyzed Addition of Thiols to N-Acyl Imines: Access to Chiral N,S-Acetals
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Nickel(0)-Catalyzed Cyclization of N-Benzoylaminals for Isoindolinone Synthesis
Danielle M. Shacklady-McAtee, Srimoyee Dasgupta, and Mary P. WatsonOrganic Letters2011 Article ASAPNickel(0)-Catalyzed Cyclization of N-Benzoylaminals for Isoindolinone Synthesis
Danielle M. Shacklady-McAtee, Srimoyee Dasgupta, and Mary P. WatsonOrganic Letters2011 Article ASAPA nickel(0) catalyst effectively mediates the cyclization of N-benzoyl aminals in the presence of a stoichiometric Lewis acid. This method enables preparation of a variety of isoindolinones with substitution on the benzoyl fragment and C-3 carbon. This ...
A Model for the Enantioselectivity of Imine Reactions Catalyzed by BINOL−Phosphoric Acid Catalysts
Luis Simón and Jonathan M. GoodmanThe Journal of Organic Chemistry2011 76 (6), 1775-1788A Model for the Enantioselectivity of Imine Reactions Catalyzed by BINOL−Phosphoric Acid Catalysts
Luis Simón and Jonathan M. GoodmanThe Journal of Organic Chemistry2011 76 (6), 1775-1788BINOL−phosphoric acid catalysts have been used successfully in many reactions involving imines. In this paper, we present a model, based on DFT calculations, for describing the degree and sense of the enantioselectivity of these reactions that is able to ...
Rapid Catalyst Screening by a Continuous-Flow Microreactor Interfaced with Ultra-High-Pressure Liquid Chromatography
Hui Fang, Qing Xiao, Fanghui Wu, Paul E. Floreancig and Stephen G. WeberThe Journal of Organic Chemistry2010 75 (16), 5619-5626Rapid Catalyst Screening by a Continuous-Flow Microreactor Interfaced with Ultra-High-Pressure Liquid Chromatography
Hui Fang, Qing Xiao, Fanghui Wu, Paul E. Floreancig and Stephen G. WeberThe Journal of Organic Chemistry2010 75 (16), 5619-5626A high-throughput screening system for homogeneous catalyst discovery has been developed by integrating a continuous-flow capillary-based microreactor with ultra-high-pressure liquid chromatography (UHPLC) for fast online analysis. Reactions are conducted ...
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History
- Published In Issue September 17, 2008
- Article ASAPAugust 23, 2008
- Received: May 5, 2008
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