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

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Published in Organic Letters. 2013, vol. 15, no. 9, p. 2172-2175
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).
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Other version: http://pubs.acs.org/doi/abs/10.1021/ol400697n
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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. https://archive-ouverte.unige.ch/unige:27720

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Deposited on : 2013-05-07

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