Journal ArticleDOI
Highly Enantioselective Construction of a Quaternary Carbon Center of Dihydroquinazoline by Asymmetric Mannich Reaction and Chiral Recognition
TLDR
In this paper, a chiral trifluoromethyl quaternary carbon center of dihydroquinazoline was constructed by an asymmetric Mannich reaction and chiral recognition.Abstract:
The highly enantioselective construction of a quaternary carbon center of dihydroquinazoline by an asymmetric Mannich reaction and chiral recognition are described The key transformation was to establish the chiral trifluoromethyl quaternary carbon center by a diamine-Bronsted acid-catalyzed enantioselective and regioselective Mannich reaction of a methyl ketone and 4-trifluoromethyldihydroquinazoline An unusual phenomenon of self-discrimination of enantiomers in hydrogen-bonded dimers was observed A valuable intermediate was transformed into the enantiopure HIV reverse transcriptase inhibitor DPC 083 (>999 ee) simply by reduction of the carbonyl group and elimination of the hydroxy group in hexamethylphosphoric tramide (HMPA)read more
Citations
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Synthesis of Condensed Heterocycles, Containing Partially Saturated Pyrimidine Nuclei, from Aromatic Pyrimidine Derivatives
TL;DR: In this article, the authors summarized current developments in the preparation of condensed heterocycles containing dihydropyrimidine and tetrahydropyridine nuclei by various transformations of preexisting aromatic pyrimidine derivatives and presented a variety of strategies for the construction of these highly functional heterocyclic systems.
Journal ArticleDOI
Bifunctional amino sulfonamide-catalyzed asymmetric conjugate addition to alkenyl alkynyl ketimines as enone surrogates
TL;DR: In this article, a bifunctional amino sulfonamide-catalyzed asymmetric conjugate addition of aldehydes to alkenyl alkynyl ketimines as reactive surrogates for enones has been developed.
Journal ArticleDOI
Synthesis of alkynyl Z-ketimines and their application in amine-catalyzed asymmetric Mannich reactions and conjugate addition
TL;DR: A facile and practical synthesis of various alkynyl Z-ketimines is developed, which can be used as a synthetic equivalent of alkyl ketimines and could be successfully applied in enantioselective Mannich reaction and conjugate addition catalyzed by a chiral amine with an acid functionality.
Journal ArticleDOI
A Three Component Synthesis of 2-Aryl-3-imidamide Substituted 1,2-Dihydroquinazolin-4(1H)-ones
Arkalekha Mandal,Bhisma K. Patel +1 more
Journal ArticleDOI
Synthesis of (S)-(+)-6-aryl-3-acetyl-6-trifluoromethyl-5,6-dihydropyridin-2(1H)-ones
TL;DR: In this paper, (S)-(+)-6-aryl-3-acetyl(or trifluoroacetyl)6-trifluoromethyl-5,6-dihydropyridin-2(1H)-ones.
References
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Enamine-Based Organocatalysis with Proline and Diamines: The Development of Direct Catalytic Asymmetric Aldol, Mannich, Michael, and Diels−Alder Reactions
TL;DR: The contributions of this laboratory to converting enzymatic enamines, and in some cases imines, into a versatile catalytic asymmetric strategy powered by small organic molecules are summarized.
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The direct catalytic asymmetric mannich reaction.
TL;DR: The direct catalytic asymmetric addition of unmodified carbonyl compounds to preformed or in situ-generated imines has emerged as a promising new route to optically enriched alpha- and beta-amino acid derivatives, beta-lactams, and 1,2- and gamma-aminos alcohols.
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The proline-catalyzed direct asymmetric three-component Mannich reaction: Scope, optimization, and application to the highly enantioselective synthesis of 1,2-amino alcohols
TL;DR: Proline-catalyzed direct asymmetric three-component Mannich reactions of ketones, aldehydes, and amines are developed and application to the highly enantioselective synthesis of 1,2-amino alcohols is presented.
Journal ArticleDOI
Organocatalysed asymmetric Mannich reactions.
TL;DR: This tutorial review provides an overview of the recent history of the asymmetric organocatalysed Mannich reaction, including scope and limitations, and application of different catalyst systems.
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Organocatalytic Asymmetric Mannich Reactions: New Methodology, Catalyst Design, and Synthetic Applications
Amal Ting,Scott E. Schaus +1 more
TL;DR: In this paper, the authors present the methodology and synthetic advantages achieved so far in the asymmetric Mannich reaction, and present a Microreview of the recent contributions to this process.