Journal article
Asymmetric oxidation of achiral selenides to optically active selenoxides : Stereochemistry of the allyl selenoxide-selenenate [2,3] sigmatropic rearrangement
Tetrahedron, v 41(21), pp 4747-4757
1985
Featured in Collection : UN Sustainable Development Goals @ Drexel
Abstract
Asymmetric oxidation of methyl phenyl selenide (
3
), under anhydrous conditions, by chiral 2-sulfonyloxaziridines,
1–2
, gives optically active methyl phenyl selenoxide (8.1–9.3% ee). The stereochemistry of the selenoxide is determined by the configuration of the oxaziridine three membered ring with non-bonded steric interactions responsible for the chiral recognition. Asymmetric oxidation of E-phenyl cinnamyl selenide (
7
) by
1–2
affords optically active l-phenylallyl alcohol (
9
). A concerted [2,3] sigmatropic rearrangement via an exo transition state is proposed.
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Details
- Title
- Asymmetric oxidation of achiral selenides to optically active selenoxides : Stereochemistry of the allyl selenoxide-selenenate [2,3] sigmatropic rearrangement
- Creators
- Franklin A. Davis - Drexel UniversityOrum D. Stringer - Drexel UniversityJohn P. McCauley - Drexel University
- Publication Details
- Tetrahedron, v 41(21), pp 4747-4757
- Publisher
- Elsevier
- Resource Type
- Journal article
- Language
- English
- Academic Unit
- [Retired Faculty]
- Web of Science ID
- WOS:A1985AUT7600003
- Scopus ID
- 2-s2.0-27144488353
- Other Identifier
- 991019173868904721
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InCites Highlights
Data related to this publication, from InCites Benchmarking & Analytics tool:
- Web of Science research areas
- Chemistry, Organic