Silicon-assisted propargylic transfer to aldehydes

Chem Commun (Camb). 2004 Nov 7:(21):2456-7. doi: 10.1039/b411653d. Epub 2004 Sep 21.

Abstract

A new and efficient method of obtaining homopropargylic alcohols via homopropargylic transfer from the allenic alcohol to various aldehydes in the presence of Lewis acid catalysts is described; stereochemical studies have shown that this process is the first oxonium [3,3]-sigmatropic rearrangement of an allenic alcohol to a homopropargylic alcohol in the presence of aldehydes and Lewis acid.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemistry*
  • Alkynes / chemical synthesis*
  • Alkynes / chemistry
  • Molecular Structure
  • Propanols / chemistry
  • Silicon / chemistry*

Substances

  • Aldehydes
  • Alkynes
  • Propanols
  • propargyl alcohol
  • Silicon