Versatile Scope of a Masked Aldehyde Nitrone in 1,3-Dipolar Cycloadditions

Org Lett. 2015 Nov 20;17(22):5550-3. doi: 10.1021/acs.orglett.5b02662. Epub 2015 Nov 2.

Abstract

A new masked aldehyde-containing nitrone 1 that is easily available through a facile one-step procedure has been developed. It undergoes a [3 + 2]-thermal cycloaddition with a wide range of dipolarophiles, affording isoxazolidine cycloadducts that are suitable for versatile postcycloaddition modifications. The acetal cycloadducts are acid-stable, but allow for acetal hydrolysis under mildly basic conditions. The isoxazolidine ring can be opened via an efficient one-pot procedure to give amine-protected γ-alcohols that can be further converted to furanose derivatives.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetals
  • Aldehydes / chemistry*
  • Amines
  • Cyclization
  • Cycloaddition Reaction
  • Isoxazoles / chemistry
  • Molecular Structure
  • Nitrogen Oxides / chemistry*
  • Stereoisomerism

Substances

  • Acetals
  • Aldehydes
  • Amines
  • Isoxazoles
  • Nitrogen Oxides
  • nitrones