Enantioselective [3+2] cycloaddition of azomethine ylides and aldehydes via Ni/bis(oxazoline)-catalyzed ring opening of N-tosylaziridines through a chirality transfer approach

Xingxing Wu; Wei Zhou; Hai-Hong Wu; Junliang Zhang

doi:10.1039/c7cc02906c

Enantioselective [3+2] cycloaddition of azomethine ylides and aldehydes via Ni/bis(oxazoline)-catalyzed ring opening of N-tosylaziridines through a chirality transfer approach

Chem Commun (Camb). 2017 May 18;53(41):5661-5664. doi: 10.1039/c7cc02906c.

Authors

Xingxing Wu¹, Wei Zhou, Hai-Hong Wu, Junliang Zhang

Affiliation

¹ Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, Shanghai 200062, China. jlzhang@chem.ecnu.edu.cn.

PMID: 28485434
DOI: 10.1039/c7cc02906c

Abstract

A diastereo- and enantioselective formal [3+2] cycloaddition of N-tosylaziridines and aldehydes catalyzed by a Ni(ii)-bisoxazoline complex has been accomplished. The 1,3-oxazolidine products are obtained with high diastereoselectivity, good yields (up to 99%) and high ee values (up to 96% ee). The challenging long distant stereocenter control is achieved by a chirality transfer approach.