Highly enantioselective synthesis of gamma-hydroxy-alpha,beta-acetylenic esters catalyzed by a beta-sulfonamide alcohol

Org Lett. 2007 Jun 7;9(12):2329-32. doi: 10.1021/ol070692x. Epub 2007 May 11.

Abstract

This work concerns the asymmetric addition of methyl propiolate to aldehydes with 1,2-dimethoxyethane (DME) as additive and beta-sulfonamide alcohol titanium complex as a catalyst. The reactions proceeded under mild conditions and gave the highly functionalized chiral propargylic alcohols with high ee values and good yields. Differences between three types of ligands have also been discussed.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alcohols / chemistry*
  • Alkynes / chemical synthesis*
  • Alkynes / chemistry
  • Catalysis
  • Esters / chemical synthesis*
  • Esters / chemistry
  • Molecular Structure
  • Organometallic Compounds / chemistry*
  • Stereoisomerism
  • Sulfonamides / chemistry*
  • Titanium / chemistry*

Substances

  • Alcohols
  • Alkynes
  • Esters
  • Organometallic Compounds
  • Sulfonamides
  • Titanium