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Highly E ‐Selective and Enantioselective Michael Addition to Electron‐Deficient Internal Alkynes Under Chiral Iminophosphorane Catalysis
Author(s) -
Uraguchi Daisuke,
Yamada Kohei,
Ooi Takashi
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201503928
Subject(s) - enantioselective synthesis , chemistry , chirality (physics) , nucleophile , michael reaction , conjugate , catalysis , olefin fiber , combinatorial chemistry , optically active , axial chirality , stereochemistry , organic chemistry , mathematical analysis , chiral symmetry breaking , physics , mathematics , quantum mechanics , nambu–jona lasinio model , quark
A highly E‐selective and enantioselective conjugate addition of 2‐benzyloxythiazol‐5(4H)‐ones to β‐substituted alkynyl N‐acyl pyrazoles is achieved under the catalysis of a P ‐spiro chiral iminophosphorane. Simultaneous control of the newly generated central chirality and olefin geometry is possible with a wide array of the alkynyl Michael acceptors possessing different aromatic and aliphatic β‐substituents, as well as the various α‐amino acid‐derived thiazolone nucleophiles. This protocol provides access to structurally diverse, optically active α‐amino acids bearing a geometrically defined trisubstituted olefinic component at the α‐position.