Issue 41, 2017

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

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.

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

Supplementary files

Article information

Article type
Communication
Submitted
18 Apr 2017
Accepted
03 May 2017
First published
03 May 2017

Chem. Commun., 2017,53, 5661-5664

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

X. Wu, W. Zhou, H. Wu and J. Zhang, Chem. Commun., 2017, 53, 5661 DOI: 10.1039/C7CC02906C

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