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

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.