☆ 4.8 Article

Highly Diastereo- and Enantioselective Palladium-Catalyzed [3+2] Cycloaddition of Vinyl Aziridines and α,β-Unsaturated Ketones

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2015)

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Volume 54, Issue 5, Pages 1604-1607

Publisher

WILEY-V C H VERLAG GMBH

DOI: 10.1002/anie.201409467

Keywords

asymmetric catalysis; cycloaddition; heterocycles; palladium; synthetic methods

Categories

Chemistry, Multidisciplinary

Funding

Major Basic Research Development Program [2011CB833300]
NNSF China [21372242, 21272251, 21032007]
Chinese Academy of Sciences
Croucher Foundation of Hong Kong

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Abstract

A palladium-catalyzed asymmetric [3+2] cycloaddition reaction of vinylaziridines with alpha,beta-unsaturated ketones, wherein the alkenes have a single activator, is realized in high diastereo- and enantioselectivity, thus affording 3,4-disubstituted pyrrolidines in high yields with excellent ee values. The introduction of a methyl group at C1 of the vinyl group the vinylaziridines greatly improves the stereochemistry of the reaction. A plausible transition state is proposed.

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