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The Reaction of Some α-Oxygenated Cyclic Ketones with Sulfur Ylides

✍ Scribed by Marschner, Christoph ;Baumgartner, Judith ;Griengl, Herfried

Publisher
John Wiley and Sons
Year
1994
Tongue
English
Weight
604 KB
Volume
1994
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

Cyclopentanones 1, 4 and 7, as well as uloses 11, 14, 17, and 20, all possessing an oxygen atom in α‐position with respect to the carbonyl group, have been allowed to react with dimethylsulfonium and dimethyloxosulfonium methylides. It has been found that the nucleophilic attack can be directed by the neighboring axial oxygen substituent, which leads to unusual selectivity compared to normal nucleophilic attack. The isomeric epoxides resulting from sterically directed attack have been prepared in all cases either by reaction with bromomethyllithium or by using an olefination‐epoxidation procedure.

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