2-Vinyl Threoninol Derivatives via Acid-Catalyzed Allylic Substitution of Bisimidates

J Org Chem. 2015 Jun 5;80(11):5934-43. doi: 10.1021/acs.joc.5b00529. Epub 2015 May 18.

Abstract

A diastereoselective synthesis of 4-vinyl oxazolines syn-2 was developed based on an acid-catalyzed cyclization of bistrichloroacetimidates (E)-1. The reaction likely involves an allyl carbenium ion intermediate in which the adjacent stereocenter directs the stereoselectivity for C-N bond formation. Oxazolines syn-2 were transformed to C-quaternary threoninol, threoninal, and threonine derivatives which can be further incorporated into complex natural compounds.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Allyl Compounds / chemistry*
  • Amino Alcohols / chemistry*
  • Butylene Glycols / chemistry*
  • Cyclization
  • Imidoesters / chemical synthesis*
  • Imidoesters / chemistry
  • Molecular Structure
  • Oxazoles / chemical synthesis*
  • Oxazoles / chemistry
  • Stereoisomerism
  • Vinyl Compounds / chemistry*

Substances

  • 2-vinyl threoninol
  • Allyl Compounds
  • Amino Alcohols
  • Butylene Glycols
  • Imidoesters
  • Oxazoles
  • Vinyl Compounds
  • threoninol