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A mild and efficient synthesis of thiolesters from alcohols

โœ Scribed by Jacques Yves Gauthier; France Bourdon; Robert Norman Young

Book ID
104218041
Publisher
Elsevier Science
Year
1986
Tongue
French
Weight
217 KB
Volume
27
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

Sumnary:

Numerous functionally diverse thiolesters are prepared in high yield in a mild "one-pot" synthesis from activated alcohols and thlolacids under Lewis acid catalysis.

Among the large number of methods available for the synthesis of thiols those which make use of alkenes and alkyl halides as starting materials have been the most extensively studied. 2 In principle, many are simple processes but the further reaction of the initially formed thiols to give sulfides or disulfides often serves to severely limit their utility as synthetic methods.

Other routes, such as by the direct reaction between alcohols and hydrogen sulfide or phosphorus pentasulfide have also been reported.

3 They however

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A new, highly efficient method for the c
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Various alcohols were converted to their corresponding thiolacetates by treatment with triphenylphosphine and diisopropyl azodicarboxylate in the presence of thiolacetlc acid. The overall conversion was both highly efficient (89-99X yields) and stereoselective (99.5% inversion).