Organic Letters 2011-06-17

Catalytic asymmetric vinylogous Mannich-type (AVM) reaction of nonactivated α-angelica lactone.

Lin Zhou, Lili Lin, Jie Ji, Mingsheng Xie, Xiaohua Liu, Xiaoming Feng

Index: Org. Lett. 13(12) , 3056-9, (2011)

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Abstract

A direct highly diastereo- and enantioselective asymmetric vinylogous Mannich-type (AVM) reaction of aldimines with nonactivated natural α-angelica lactone has been successfully developed. It was demonstrated that the nonactivated natural α-angelica lactone is a useful vinylogous nucleophile to give the chiral δ-amino γ,γ-disubstituted butenolide carbonyl derivatives. The N,N'-dioxide L2-Sc(III) complex is efficient toward the obtention of a range of corresponding products with adjacent quaternary and tertiary stereocenters in excellent dr and ee values.© 2011 American Chemical Society