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Diastereoselective addition reactions of racemic chiral vinyl sulfimides
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UNSPECIFIED (2000) Diastereoselective addition reactions of racemic chiral vinyl sulfimides. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 (1). pp. 79-87. ISSN 0300-922X
Full text not available from this repository.Abstract
S-Aryl S-vinyl sulfimides are prepared by a new method via Horner-Wadsworth-Emmons reagents generated in situ. Lewis acid-catalysed Diels-Alder reaction of S-ethenyl-S-phenyl-N-tosylsulfimide with cyclopentadiene leads to the endo anti product with good diastereofacial and endo-exo selectivities. A range of alcohols and amines, with the limitation that they be practically usable in large excess, add to beta-aryl vinyl sulfimides with modest diastereoselectivity. The major products of both the cycloaddition and the nucleophilic additions are rationalised by a model invoking addition to the least-hindered face of the s-cis conformation of the vinyl sulfimide.
| Item Type: | Journal Article |
|---|---|
| Subjects: | Q Science > QD Chemistry |
| Journal or Publication Title: | JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 |
| Publisher: | ROYAL SOC CHEMISTRY |
| ISSN: | 0300-922X |
| Date: | 7 January 2000 |
| Number: | 1 |
| Number of Pages: | 9 |
| Page Range: | pp. 79-87 |
| Publication Status: | Published |
| URI: | http://wrap.warwick.ac.uk/id/eprint/13770 |
Data sourced from Thomson Reuters' Web of Knowledge
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