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A novel and efficient method for the preparation of asymmetric dithioacetals

✍ Scribed by J.Y. Gauthier; T. Henien; L. Lo; M. Thérien; R.N. Young

Publisher
Elsevier Science
Year
1988
Tongue
French
Weight
228 KB
Volume
29
Category
Article
ISSN
0040-4039

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✦ Synopsis

Aldehydes and ketones react with one equivalent each of thiols and thiolacetic acid under acid catalysis to yield almost exclusively the mixed alkylthio-(or arylthio-) acvlthioacetals. Reaction of the mixed thioacetal with a nucleoohile (such as NaOMe) liberates the thiolate anion which can be trapped with a variety'of electrophiles to provide asymmetric dithioacetals in high yields. Thioacetals and thioketals are an important class of functional groups best known as protecting groups for aldehydes and ketones and, in the case of thioacetals, as units which can serve as acyl anion equivalents. This unit has also recently found considerable use in the medicinal chemistry of leukotriene antagonists where bis-thioalkanoic acid acetals have served as mimetics of the diacid polar portion (Cl-C61 of leukotriene Cl4 or leukotriene

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