Diastereoselective synthesis of 2-phenylselenenyl-1,3-anti-diols and 2-phenylselenenyl-1,3-anti-azido-alcohols via hydroxy and azido-selenenylation reactions

Molecules. 2005 Feb 28;10(2):383-93. doi: 10.3390/10020383.

Abstract

A method to synthesize 2-phenylselenenyl-1,3-anti-diols and 2-phenyl- selenenyl-1,3-anti-azidoalcohols via hydroxy- or azido-selenenylation of trans-allylic alcohols is reported. Moreover, the first example of hydroxyl-selenenylation of an allylic azide is presented. Yields ranging from moderate to good and diastereomeric ratios up to 95:5 are achieved.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alcohols / chemical synthesis*
  • Alcohols / chemistry*
  • Hydroxylation
  • Models, Biological
  • Organoselenium Compounds / chemical synthesis*
  • Organoselenium Compounds / chemistry*
  • Propanols / chemistry
  • Selenic Acid
  • Selenium Compounds / chemistry*
  • Stereoisomerism
  • Substrate Specificity

Substances

  • Alcohols
  • Organoselenium Compounds
  • Propanols
  • Selenium Compounds
  • allyl alcohol
  • Selenic Acid