The conformational bias of aryl, arylsulfonyl geminally substituted tertiary carbon centers: applications in substrate-based stereocontrol
| Autor: | Jeremy P. Scott, Jennifer R. Chilenski, Andrew D. Gibb, Antony J. Davies, Ulf-H. Dolling, David R. Lieberman, Steven F. Oliver, Karel M. J. Brands, Peter R. Mullens, Sarah E. Brewer |
|---|---|
| Rok vydání: | 2006 |
| Předmět: |
chemistry.chemical_classification
Ketone Nitrile Stereochemistry Aryl Organic Chemistry Molecular Conformation Substrate (chemistry) Alkenes Crystallography X-Ray Biochemistry Hydrocarbons Aromatic Cycloaddition chemistry.chemical_compound chemistry Intramolecular force Sulfones Physical and Theoretical Chemistry Acrylonitrile Single crystal |
| Zdroj: | Organicbiomolecular chemistry. 4(9) |
| ISSN: | 1477-0520 |
| Popis: | Intramolecular nitrile oxide–olefin cycloaddition to form hexahydrobenzisoxazole 14, which engenders a phenylsulfonyl, 2,5-difluorophenyl geminally substituted carbon substructure, proceeds with up to 99% ds. A rationalization of the high level of substrate-based stereo-induction observed in this and related ketone and acrylonitrile metallohydride reductions, supported by single crystal X-ray crystallography, is presented. |
| Databáze: | OpenAIRE |
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