Jump to Main Content
Development of the Enantioselective Addition of Ethyl Diazoacetate to Aldehydes: Asymmetric Synthesis of 1,2-Diols
- Trost, Barry M., Malhotra, Sushant, Koschker, Philipp, Ellerbrock, Pascal
- Journal of the American Chemical Society 2012 v.134 no.4 pp. 2075-2084
- aldehydes, enantiomers, glycols
- 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.