A regio- and diastereoselective intramolecular nitrone cycloaddition for practical 3- and 2,3-disubstituted piperidine synthesis from gamma-butyrolactone

J Org Chem. 2009 Jan 2;74(1):254-63. doi: 10.1021/jo8018285.

Abstract

A fast and efficient route for diversity-oriented synthesis of 3- and 2,3-disubstituted piperidines, featuring an intramolecular nitrone cycloaddition with high regio- and diastereoselectivity, was achieved in six steps and 36-66% overall yield from commercially available gamma-butyrolactone or 1,4-butanediol. A new N-alkenyl nitrone enoate was used in this intramolecular nitrone cycloaddition, and the regioselectivity, diastereoselectivity, and reversibility of this cycloaddition were investigated.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 4-Butyrolactone / chemistry*
  • Cyclization
  • Molecular Structure
  • Nitrogen Oxides / chemistry*
  • Piperidines / chemical synthesis*
  • Piperidines / chemistry
  • Stereoisomerism

Substances

  • Nitrogen Oxides
  • Piperidines
  • nitrones
  • 4-Butyrolactone