Direct Catalytic Asymmetric Mannich-Type Reactions of γ-Butenolides: Effectiveness of Brønsted Acid in Chiral Metal Catalysis
- 7 May 2008
- journal article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 10 (11) , 2319-2322
- https://doi.org/10.1021/ol800756r
Abstract
Direct catalytic asymmetric Mannich-type reactions of γ-butenolides are described. A chiral Lewis acid/amine base/Brønsted acid combination was used to catalyze a γ-addition of γ-butenolides to N-diphenylphosphinoyl imines, affording the products in up to >99% yield, anti/syn = >97:3, and 84% ee. The use of a catalytic amount of TfOH in addition to La(OTf)3/Me-PyBox/TMEDA was important for improving yield and stereoselectivity.Keywords
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