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Direct Catalytic Asymmetric Synthesis of N‐Heterocycles from Commodity Acid Chlorides by Employing α,β‐Unsaturated Acylammonium Salts
Author(s) -
Vellalath Sreekumar,
Van Khoi N.,
Romo Daniel
Publication year - 2013
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201306050
Subject(s) - cinchona , nucleophile , catalysis , reactivity (psychology) , chemistry , organic chemistry , commodity , michael reaction , enantioselective synthesis , combinatorial chemistry , business , finance , medicine , alternative medicine , pathology
Taming the beast, asymmetrically : Modulation of the reactivity of acid chlorides, using cinchona alkaloid catalysts, results in chiral α,β‐unsaturated acylammoniums, which react with nucleophiles enantioselectively to give pyrrolidinones, piperid‐2‐ones, and dihydropyridinones. This nucleophile‐catalyzed Michael/proton transfer/lactamization or lactonization organocascade leads to chiral intermediates previously employed for the synthesis of bioactive pharmaceuticals.