Direct Catalytic Asymmetric Mannich-Type Reactions of g-Butenolides: Effectiveness of Bronsted Acid in Chiral Metal Catalysis.

[摘要]：Direct catalytic asym. Mannich-type reactions of g-butenolides I (R = H, Me) are described. A chiral Lewis acid/amine base/Bronsted acid combination was used to catalyze a g-addn. of g-butenolides to N-diphenylphosphinoyl imines R1CH:NP(:O)Ph2 (R1 = Ph, 4-ClC6H4, 2-thienyl, n-Bu, etc.) affording the products II in up to >99% yield, anti/syn = >97:3, and 84% ee. The use of a catalytic amt. of TfOH in addn. to La(OTf)3/Me-PyBox/TMEDA was important for improving yield and stereoselectivity.

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