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Asymmetric Synthesis of Isothiazoles through Cu Catalysis: Direct Catalytic Asymmetric Conjugate Addition of Allyl Cyanide to α,β‐Unsaturated Thioamides
Author(s) -
Yanagida Yuka,
Yazaki Ryo,
Kumagai Naoya,
Shibasaki Masakatsu
Publication year - 2011
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.201102467
Subject(s) - catalysis , lewis acids and bases , electrophile , intramolecular force , cyanide , conjugate , chemistry , thioamide , combinatorial chemistry , medicinal chemistry , organic chemistry , mathematics , mathematical analysis
Twice the catalyst : The simultaneous activation of an allyl cyanide (pronucleophile) and an α,β‐unsaturated thioamide (electrophile) was achieved using a Cu‐based soft Lewis acid/hard Brønsted base cooperative catalyst, thus resulting in the formation of enethioamides 1 in a highly enantio‐ and Z ‐selective manner (see scheme). The sequential Cu‐catalyzed intramolecular cyclization gave rise to enantioenriched fused isothiazoles 2 .