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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.
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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 | ||||
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Subjects: | Q Science > QD Chemistry | ||||
Journal or Publication Title: | JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | ||||
Publisher: | ROYAL SOC CHEMISTRY | ||||
ISSN: | 0300-922X | ||||
Official Date: | 7 January 2000 | ||||
Dates: |
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Number: | 1 | ||||
Number of Pages: | 9 | ||||
Page Range: | pp. 79-87 | ||||
Publication Status: | Published |
Data sourced from Thomson Reuters' Web of Knowledge
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