Issue 1, 2014

Chiral primary amine catalysed asymmetric conjugate addition of azoles to α-substituted vinyl ketones

Abstract

We report here the first effective example of asymmetric conjugate addition–protonation reactions of azoles to vinyl ketones by chiral primary amine catalysis. High enantioselectivity can be easily achieved by screening different primary amine catalysts, and the Curtin–Hammett control in the C–N bond formation step was verified by DFT calculations to account for the observed stereoselectivity.

Graphical abstract: Chiral primary amine catalysed asymmetric conjugate addition of azoles to α-substituted vinyl ketones

Supplementary files

Article information

Article type
Research Article
Submitted
05 Nov 2013
Accepted
28 Nov 2013
First published
19 Dec 2013

Org. Chem. Front., 2014,1, 68-72

Chiral primary amine catalysed asymmetric conjugate addition of azoles to α-substituted vinyl ketones

N. Fu, L. Zhang, S. Luo and J. Cheng, Org. Chem. Front., 2014, 1, 68 DOI: 10.1039/C3QO00027C

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