Asymmetric [3 + 2] cycloaddition of donor-acceptor aziridines with aldehydes via carbon-carbon bond cleavage
Yuting Liao1, Xiaohua Liu1, Yu Zhang1
1Key Laboratory of Green Chemistry & Technology , Ministry of Education , College of Chemistry , Sichuan University , Chengdu 610064 , China . Email: liuxh@scu.edu.cn ; Email: xmfeng@scu.edu.cn ; ; Tel: +86 28 85418249.
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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