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Development of the Enantioselective Addition of Ethyl Diazoacetate to Aldehydes: Asymmetric Synthesis of 1,2-Diols

Author:
Trost, Barry M., Malhotra, Sushant, Koschker, Philipp, Ellerbrock, Pascal
Source:
Journal of the American Chemical Society 2012 v.134 no.4 pp. 2075-2084
ISSN:
1520-5126
Subject:
aldehydes, enantiomers, glycols
Abstract:
A novel synthetic strategy toward the asymmetric synthesis of vicinal diols bearing a tertiary center is presented. The method encompasses the dinuclear Mg-catalyzed asymmetric addition of ethyl diazoacetate into several aldehydes, oxidation of the diazo functionality, and diastereoselective alkyl transfer of various organometallics into the resulting chiral β-hydroxy-α-ketoesters to afford a diverse range of 1,2-diols in high yield, diastereoselectivity, and chirality transfer.
Agid:
5386745