- Catalytic asymmetric vinylogous Mannich-type (AVM) reaction of nonactivated α-angelica lactone.
Catalytic asymmetric vinylogous Mannich-type (AVM) reaction of nonactivated α-angelica lactone.
Organic letters (2011-05-21)
Lin Zhou, Lili Lin, Jie Ji, Mingsheng Xie, Xiaohua Liu, Xiaoming Feng
PMID21595425
초록
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.