Development of the enantioselective addition of ethyl diazoacetate to aldehydes: asymmetric synthesis of 1,2-diols

J Am Chem Soc. 2012 Feb 1;134(4):2075-84. doi: 10.1021/ja206995s. Epub 2012 Jan 18.

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.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Alcohols / chemical synthesis*
  • Alcohols / chemistry
  • Aldehydes / chemistry*
  • Diazonium Compounds / chemistry*
  • Molecular Structure
  • Stereoisomerism

Substances

  • Alcohols
  • Aldehydes
  • Diazonium Compounds
  • diazoacetic ester