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Direct Catalytic Asymmetric Vinylogous Mannich‐Type Reaction of γ‐Butenolides with Ketimines
Author(s) -
Yin Liang,
Takada Hisashi,
Kumagai Naoya,
Shibasaki Masakatsu
Publication year - 2013
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.201303119
Subject(s) - stereocenter , adduct , catalysis , chemistry , sulfur , combinatorial chemistry , lewis acids and bases , computer science , organic chemistry , enantioselective synthesis , stereochemistry
A cooperative catalyst consisting of a soft Lewis acid and a hard Brønsted base promoted the title reaction. The N ‐thiophosphinoyl group on the ketimines was critical to surpass the high activation barrier through the soft–soft interaction of sulfur and copper. Mannich adducts with a tetrasubstituted stereogenic center were produced with excellent diastereo‐ and enantioselectivities. TANIAPHOS= ferrocenyl ligand.