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Scientific article
English

Highly Diastereo- and Enantioselective Organocatalytic Domino Michael/Aldol Reaction of Acyclic 3-Halogeno-1,2-Diones to α,β-Unsaturated Aldehydes

Published inOrganic letters, vol. 15, no. 9, p. 2172-2175
Publication date2013
Abstract

The first organocatalytic diastereo- and enantioselective domino Michael/aldol reaction of 3-halogeno-1,2-diones to α,β-unsaturated aldehydes has been achieved. This transformation tolerates a large variety of electronically different substituents on both reactive partners and allows the synthesis of challenging cyclopentanone derivatives with four contiguous stereogenic centers in excellent diastereoselectivities (>20:1 dr) as well as good yields (69–97%), and enantioselectivities (up to 94% ee).

Citation (ISO format)
LEFRANC, Alice, GUENEE, Laure, ALEXAKIS, Alexandre. Highly Diastereo- and Enantioselective Organocatalytic Domino Michael/Aldol Reaction of Acyclic 3-Halogeno-1,2-Diones to α,β-Unsaturated Aldehydes. In: Organic letters, 2013, vol. 15, n° 9, p. 2172–2175. doi: 10.1021/ol400697n
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ISSN of the journal1523-7052
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Creation05/03/2013 9:12:00 AM
First validation05/03/2013 9:12:00 AM
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