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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Title		Highly Diastereo- and Enantioselective Organocatalytic Domino Michael/Aldol Reaction of Acyclic 3-Halogeno-1,2-Diones to α,β-Unsaturated Aldehydes
Authors		Lefranc, Alice Guenee, Laure Alexakis, Alexandre
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).
Identifiers		DOI: 10.1021/ol400697n
Full text		Article (Published version) (374 Kb) - Limited access to UNIGE
Structures		Faculté des sciences / Section de chimie et biochimie / Département de chimie organique
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 https://archive-ouverte.unige.ch/unige:27720

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Deposited on : 2013-05-07

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