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A cross-aldol type reaction of alkenyl sulfide with trimethylsilyl enol ether.

✍ Scribed by Takeshi Takeda; Yuichiro Kaneko; Tooru Fujiwara

Publisher
Elsevier Science
Year
1986
Tongue
French
Weight
191 KB
Volume
27
Category
Article
ISSN
0040-4039

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✦ Synopsis

Phenylthio ketones were obtained in good yields by the successive treatment of alkenyl sulfides with TiC14-ROH (R= Me or t-Bu) and trimethylsilyl enol ethers. Alkenyl sulfides are regarded as "masked carbonyl compounds" and various methods for the preparation of them including the alkylation of 1-(alkylthio)vinyllithium reagents were reported. 1) Although several reagents are developed for the hydrolysis of alkenyl sulfides to the corresponding carbonyl compounds, 2) it is well known that alkenyl sulfides are rather unsusceptible to hydrolysis as compared with other masked carbonyl compounds such as thioacetals. Therefore, it is important to investigate their direct reactions with nucleophilic reagents to extend the application of alkenyl sulfides in organic synthesis. In this communication, we wish to describe a simple procedure for a cross-aldol type reaction of alkenyl sulfides (1) with trimethylsilyl enol ethers (2).

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