Asymmetric [3 + 2] cycloaddition of donor-acceptor aziridines with aldehydes via carbon-carbon bond cleavage

Chemical Science
Yuting LiaoXiaoming Feng

Abstract

An enantioselective [3 + 2] annulation of donor-acceptor aziridines with aldehydes has been realized using a Nd(OTf)3/N,N'-dioxide/LiNTf2 catalyst system, providing various chiral cis-1,3-oxazolidines in moderate to good yields with high levels of stereocontrol. A relay catalytic process is proposed where LiNTf2 promotes the formation of azomethine ylide intermediates, and a chiral Nd(iii)-N,N'-dioxide complex accelerates the asymmetric cycloaddition.

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Citations

Nov 20, 2016·Chemistry : a European Journal·Guojin WangXiaoming Feng
Nov 5, 2019·European Journal of Organic Chemistry·Guilherme L TripodiJana Roithová
Oct 3, 2017·Accounts of Chemical Research·Xiaohua LiuXiaoming Feng
Nov 14, 2018·Journal of the American Chemical Society·Pei-Jun YangZhuo Chai
Oct 8, 2021·Chemical Communications : Chem Comm·Haizhen LiWei-Dong Z Li

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Methods Mentioned

BETA
X-ray

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