Article
One-pot synthesis of vinylisoxazolidines from simple hydroxylamines and conjugated carbonyls
Tetrahedron Letters
(2017)
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.
Keywords
- Isoxazolidines,
- Vinylnitrones,
- Dipolar cycloaddition,
- Dipolarophiles
Disciplines
Publication Date
December 13, 2017
DOI
10.1016/j.tetlet.2017.10.076
Citation Information
Dylan J. Quinn, Lauren N. Tumbelty, Erica M. Moscarello, Alyson N. Paneque, et al.. "One-pot synthesis of vinylisoxazolidines from simple hydroxylamines and conjugated carbonyls" Tetrahedron Letters Vol. 58 Iss. 50 (2017) p. 4682 - 4686 ISSN: 0040-4039 Available at: http://works.bepress.com/gustavo-moura-letts/9/