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Catalytic Asymmetric Vinylogous Mannich-type (AVM) Reaction of Nonactivated α-Angelica Lactone

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posted on 17.06.2011, 00:00 authored by Lin Zhou, Lili Lin, Jie Ji, Mingsheng Xie, Xiaohua Liu, Xiaoming Feng
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–ScIII complex is efficient toward the obtention of a range of corresponding products with adjacent quaternary and tertiary stereocenters in excellent dr and ee values.