Highly diastereoselective preparation of aldol products using new functionalized allylic aluminum reagents

Org Lett. 2014 Feb 7;16(3):956-9. doi: 10.1021/ol403692k. Epub 2014 Jan 30.

Abstract

Chloro-substituted triethylsilyl enol ethers derived from cyclohexanone and related ketones are converted with aluminum powder in the presence of indium trichloride to functionalized allylic aluminum reagents which represent a new type of synthetic equivalent of metal enolates. These allylic organometallics undergo highly diastereoselective additions to aldehydes and methyl aryl ketones, giving aldol products with a β-quaternary center.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aluminum / chemistry*
  • Cyclohexanones / chemistry*
  • Ethers / chemistry*
  • Indicators and Reagents / chemistry*
  • Molecular Structure
  • Organometallic Compounds / chemistry*
  • Organosilicon Compounds / chemistry*
  • Stereoisomerism

Substances

  • Cyclohexanones
  • Ethers
  • Indicators and Reagents
  • Organometallic Compounds
  • Organosilicon Compounds
  • Aluminum