Diastereoselective addition reactions of racemic chiral vinyl sulfimides
UNSPECIFIED. (2000) Diastereoselective addition reactions of racemic chiral vinyl sulfimides. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 (1). pp. 79-87. ISSN 0300-922XFull text not available from this repository.
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|
|Date:||7 January 2000|
|Number of Pages:||9|
|Page Range:||pp. 79-87|
Actions (login required)