Direct Catalytic Asymmetric Vinylogous Mannich‐Type Reaction of γ‐Butenolides with Ketimines | Zendy

Yin Liang | Zendy; Takada Hisashi | Zendy; Kumagai Naoya | Zendy; Shibasaki Masakatsu | Zendy

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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.

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