Journal article
Metal-hydride reduction of isoxazoline-3-carboxylate esters
Tetrahedron, v 42(19), pp 5267-5272
1986
Featured in Collection : UN Sustainable Development Goals @ Drexel
Abstract
The reduction of a series of isoxazolino-3-carboxylate esters with sodium borohydride gave 3-(hydroxymethyl)isoxazolines in 34–98% yield. Reduction with DIBAH gave isoxazoline-3-carboxaldehydes in 63 and 85% yields for the two reactions studied. Isoxazoline-3-carboxaldehydes could also be prepared by Swern oxidation of the corresponding 3-(hydroxymethyl)isoxazolines. The hydroxyl group of 3-(hydroxymethyl)isoxazoline
11b
was silylated and the endocyclic double bond was cleaved by ozonolysis to produce a monosilylated triol.
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Details
- Title
- Metal-hydride reduction of isoxazoline-3-carboxylate esters
- Creators
- Patrizia Caldirola - University of MilanMarco De Amici - University of MilanCarlo De Micheli - University of MilanPeter A. Wade - Drexel UniversityDavid T. Price - Drexel UniversityJames F. Bereznak - Drexel University
- Publication Details
- Tetrahedron, v 42(19), pp 5267-5272
- Publisher
- Elsevier
- Resource Type
- Journal article
- Language
- English
- Academic Unit
- [Retired Faculty]
- Web of Science ID
- WOS:A1986E483600003
- Scopus ID
- 2-s2.0-0006184874
- Other Identifier
- 991019173722304721
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- Collaboration types
- Domestic collaboration
- International collaboration
- Web of Science research areas
- Chemistry, Organic