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Asymmetric Synthesis of Dihydropyranones from Ynones by Sequential Copper(I)‐Catalyzed Direct Aldol and Silver(I)‐Catalyzed Oxy‐Michael Reactions
Author(s) -
Shi ShiLiang,
Kanai Motomu,
Shibasaki Masakatsu
Publication year - 2012
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.201109209
Subject(s) - aldol reaction , chemoselectivity , michael reaction , catalysis , chemistry , copper , organic chemistry , combinatorial chemistry
Ynones as diene surrogates : The asymmetric synthesis of enantiomerically enriched substituted dihydropyranones is described. The products are obtained in two steps by a copper(I)‐catalyzed direct aldol reaction of ynones followed by a silver‐catalyzed oxy‐Michael reaction. This easy method is compatible with both aromatic and aliphatic substrates, and provides excellent chemoselectivity under mild reaction conditions.