One-pot synthesis of vinylisoxazolidines from simple hydroxylamines and conjugated carbonyls

Dylan J. Quinn, Lauren N. Tumbelty, Erica M. Moscarello, Alyson N. Paneque, Amy H. Zinsky, Maxim P. Russ, Graham J. Haun, Nicholas A. Cinti, Ross M. Dare, Gustavo Moura-Letts

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3 Scopus citations

Abstract

Herein is reported the highly chemo- and regioselective synthesis of 3-vinyl-4-formyl and 3-vinyl-5-formylisoxazolidines from enals, hydroxylamines and dipolarophiles under thermal conditions. The reaction works in high yields for a large array of substituted enals and a variety of dipolarophiles. The reaction provides the respective isoxazolidines with high chemoselectivity, stereospecificity and diastereoselectivity without significant purification. The substitution pattern on the dipolarophile directs the regioselectivity of the reaction to provide either 3,4- or 3,5-substituted isoxazolidine isomers. This method provides access to a wide variety of highly substituted, stereochemically dense isoxazolidine scaffolds from the selective reaction of the three proposed components.

Original languageEnglish (US)
Pages (from-to)4682-4686
Number of pages5
JournalTetrahedron Letters
Volume58
Issue number50
DOIs
StatePublished - Dec 13 2017

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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