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Issue 10, 2013
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Chlorine, an atom economical auxiliary for asymmetric aldol reactions

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Abstract

An auxiliary strategy has been developed for asymmetric reactions of aldehydes in which the auxiliary itself is not chiral, but a single chlorine atom introduced via organocatalytic α-chlorination. The stereodirecting influence of the chlorine atom is then exploited prior to its removal by radical reduction. This strategy is demonstrated in the synthesis of several aldols (92–99% ee) and the natural products (+)-dihydroyashabushiketol and (+)-solistatin.

Graphical abstract: Chlorine, an atom economical auxiliary for asymmetric aldol reactions

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Article information


Submitted
19 Dec 2012
Accepted
10 Jan 2013
First published
31 Jan 2013

Org. Biomol. Chem., 2013,11, 1702-1705
Article type
Paper

Chlorine, an atom economical auxiliary for asymmetric aldol reactions

S. D. Halperin and R. Britton, Org. Biomol. Chem., 2013, 11, 1702
DOI: 10.1039/C3OB27462D

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