Issue 5, 2007

Organocatalytic enantioselective indole alkylations of α,β-unsaturated ketones

Abstract

The C3-selective enantioselective Michael-type Friedel–Crafts alkylations of indoles with nonchelating α,β-unsaturated alkyl ketones, catalysed by a chiral primary amine derived from natural cinchonine, were investigated. The reactions, in the presence of 30 mol% catalyst, were smoothly conducted at 0 to −20 °C. Moderate to good ee (47–89%) has been achieved.

Graphical abstract: Organocatalytic enantioselective indole alkylations of α,β-unsaturated ketones

Supplementary files

Article information

Article type
Paper
Submitted
13 Nov 2006
Accepted
03 Jan 2007
First published
19 Jan 2007

Org. Biomol. Chem., 2007,5, 816-821

Organocatalytic enantioselective indole alkylations of α,β-unsaturated ketones

W. Chen, W. Du, L. Yue, R. Li, Y. Wu, L. Ding and Y. Chen, Org. Biomol. Chem., 2007, 5, 816 DOI: 10.1039/B616504D

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