Asymmetric Nucleophilic Acylation via Metalated Chiral Amino Cyanides: Enantioselective Synthesis of 3‐Substituted 4‐Oxoesters by Asymmetric Michael Addition | Zendy

Enders Dieter | Zendy; Gerdes Peter | Zendy; Kipphardt Helmut | Zendy

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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.

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