Journal article
A new route to 4-oxygenated isoxazolines. Application to the synthesis of 2-deoxy-2-aminobutose derivatives
Tetrahedron letters, v 30(10), pp 1185-1188
1989
Featured in Collection : UN Sustainable Development Goals @ Drexel
Abstract
The THP ether of 4,5-dihydro-3-nitro-4-isoxazolol, prepared by a sequential nitroaldol nitrosative cyclization strategy, was converted to a 4,5-dihydro-3-(dithiolanyl)isoxazole; subsequent LBH reduction gave a 95:5 diastereomeric mixture of 2-deoxy-2-aminothreose and -erythrose derivatives, respectively, which was cyclized to a mixture of tetrahydro-2H-1,3-oxazine-2-ones.
A 3-nitro-4-oxygenated isoxazoline, prepared from CICH2CHO in 28% overall yield, was transformed to a 3-(dithiolanyl)isoxazoline. Reduction afforded γ-amino-alcohols (1–92 d.e.) and a spirotetrahydrofuran. [Display omitted]
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Details
- Title
- A new route to 4-oxygenated isoxazolines. Application to the synthesis of 2-deoxy-2-aminobutose derivatives
- Creators
- Peter A. Wade - Drexel UniversityDavid T. Price - Drexel University
- Publication Details
- Tetrahedron letters, v 30(10), pp 1185-1188
- Publisher
- Elsevier
- Resource Type
- Journal article
- Language
- English
- Academic Unit
- [Retired Faculty]
- Web of Science ID
- WOS:A1989T747700006
- Scopus ID
- 2-s2.0-0024550451
- Other Identifier
- 991019174001704721
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- Web of Science research areas
- Chemistry, Organic