Synthesis of tert-alkyl amino hydroxy carboxylic esters via an intermolecular ene-type reaction of oxazolones and enol ethers

Org Lett. 2008 Mar 6;10(5):825-8. doi: 10.1021/ol702941f. Epub 2008 Jan 31.

Abstract

tert-Alkyl amino hydroxy carboxylic acids are abundantly present within the structure of many biologically active natural products. We describe herein the synthesis of these substrates using an oxazolone-mediated ene-type reaction with enol ethers followed by NaBH4 reduction of the intermediate oxazolone.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkynes / chemical synthesis*
  • Carboxylic Acids / chemical synthesis*
  • Crystallography, X-Ray
  • Esters
  • Ethers / chemistry*
  • Ketones / chemistry*
  • Molecular Conformation
  • Molecular Structure
  • Oxazolone / analogs & derivatives*
  • Oxazolone / chemistry*

Substances

  • Alkynes
  • Carboxylic Acids
  • Esters
  • Ethers
  • Ketones
  • Oxazolone