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Asymmetric Nucleophilic Acylation via Metalated Chiral Amino Cyanides: Enantioselective Synthesis of 3‐Substituted 4‐Oxoesters by Asymmetric Michael Addition
Author(s) -
Enders Dieter,
Gerdes Peter,
Kipphardt Helmut
Publication year - 1990
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199001791
Subject(s) - enantioselective synthesis , metalation , acylation , chemistry , michael reaction , amine gas treating , nucleophile , organic chemistry , chiral auxiliary , stereochemistry , medicinal chemistry , catalysis
Surprisingly, the synthetic potential of chiral amino cyanides 1 has hardly been exploited . These compounds are readily accessible from a chiral amine and aldehydes in the presence of KCN. After metalation, they serve as chiral acyl anion equivalents and can react, for example, with α,β‐unsaturated esters to give oxoesters 2 ( ee = 90 to 96%). Up to 91% of the chiral amine can be recovered.