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Synthesis of ketene S,S-acetals from thioamides

✍ Scribed by T. Harada; Y. Tamaru; Z. Yoshida

Publisher: Elsevier Science
Year: 1979
Tongue: French
Weight: 237 KB
Volume: 20
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)95452-8

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✦ Synopsis

A new method converting thioamides to ketene S,S-acetals, which exhibits wide compatibility with olefin, ketone, ester and amide groups, has been described. Thioamides have proved to be synthetically very potential by the total synthesis of Vitamin Bl2 (construction of corrin molecule) by Woodward and Eschenmoserl and indole alkaloids by Takano et al. 2 Recently we have developed some useful reactions making use of the characteristics of thioamides; 3 the highly stereoselective coupling reaction of thioamides to give d,l-1,4-dithioamides4 and the Michael addition reaction of wide variety of organometallics to a,f+unsaturated thioamides. 5 Although in these reactions thioamides have played an important role as the latent amines, 4,6 enamines, 7 ketene S,N-acetals, 8 amides, 9 etc., almost no report has appeared concerning on the conversion of thioamides to the ordinary carbonyl compounds, such as ketones, 10 aldehydes, and esters.

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