Journal article
Benzenesulfonylcarbonitrile oxide. 5. Face selectivity of cycloaddition to chiral terminal alkenes
Tetrahedron, v 40(3), pp 601-611
1984
Featured in Collection : UN Sustainable Development Goals @ Drexel
Abstract
The diastereomer ratio for cycloaddition of benzenesulfonylcarbonitrile oxide (BSNO) to a series of (S)-vinylglycine-derived alkenes varied from 30:70 to 66:34 depending on the substitutents at the chiral center. Isomer ratios were routinely determined by
1H-NMR; isolation confirmed the results in several cases. Isomer assignment was based on comparison to acivicin where the absolute configuration has been determined by X-ray analysis. The results are interpreted as consistent with competitive cycloaddition to the alkene oriented in two differing conformations.
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Details
- Title
- Benzenesulfonylcarbonitrile oxide. 5. Face selectivity of cycloaddition to chiral terminal alkenes
- Creators
- Peter A. Wade - Drexel UniversityShankar M. Singh - Drexel UniversityM.Krishna Pillay - Drexel University
- Publication Details
- Tetrahedron, v 40(3), pp 601-611
- Publisher
- Elsevier
- Resource Type
- Journal article
- Language
- English
- Academic Unit
- [Retired Faculty]
- Web of Science ID
- WOS:A1984SF96400017
- Scopus ID
- 2-s2.0-0001612564
- Other Identifier
- 991019174749404721
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- Web of Science research areas
- Chemistry, Organic