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Direct Catalytic Asymmetric Vinylogous Conjugate Addition of Unsaturated Butyrolactones to α,β‐Unsaturated Thioamides
Author(s) -
Yin Liang,
Takada Hisashi,
Lin Shaoquan,
Kumagai Naoya,
Shibasaki Masakatsu
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201402332
Subject(s) - stereocenter , enantioselective synthesis , conjugate , catalysis , lewis acids and bases , chemistry , lactone , brønsted–lowry acid–base theory , atom economy , stereochemistry , organic chemistry , mathematics , mathematical analysis
Abstract Soft Lewis acid/Brønsted base cooperative catalysts have enabled direct catalytic asymmetric vinylogous conjugate addition of α,β‐ and β,γ‐unsaturated butyrolactones to α,β‐unsaturated thioamides with perfect atom economy. When using α‐angelica lactone and its derivatives as pronucleophiles, as little as 0.5 mol % catalyst loading was sufficient to complete the reaction necessary to construct consecutive tri‐ and tetrasubstituted stereogenic centers in a highly diastereo‐ and enantioselective fashion.