Direct Catalytic Asymmetric Vinylogous Mannich-Type Reaction of γ-Butenolides with Ketimines

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 tetrasubstitute...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2013-07, Vol.52 (28), p.7310-7313
Main Authors: Yin, Liang, Takada, Hisashi, Kumagai, Naoya, Shibasaki, Masakatsu
Format: Article
Language:English
Subjects:
4-Butyrolactone - analogs & derivatives
4-Butyrolactone - chemistry
asymmetric catalysis
atom economy
Catalysis
cooperative catalysis
Imines - chemistry
ketimines
Ketones - chemistry
Lewis Acids - chemistry
Nitriles - chemistry
Oxidation-Reduction
Stereoisomerism
synthetic methods
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Summary: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.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201303119