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Article Dans Une Revue Organic Letters Année : 2013

Synthesis of sulfonic acid derivatives by oxidative deprotection of thiols using tert-butyl hypochlorite

Résumé

Starting from alkyl halides or Michael acceptors, thioacetates were prepared in situ and further treated with t-BuOCl, affording the corresponding sulfonyl chlorides which were trapped with nucleophiles such as water, alcohol, or amines. The three steps can be achieved in a one-pot procedure. Oxidative deprotection also proved to be efficient with S-trityl and S-tert-butyl groups, making it a convenient route toward cysteic acid derivatives.

Domaines

Chimie organique
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Dates et versions

hal-00997432 , version 1 (28-05-2014)

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Citer

Yoann Joyard, Cyril Papamicaël, Pierre Bohn, Laurent Bischoff. Synthesis of sulfonic acid derivatives by oxidative deprotection of thiols using tert-butyl hypochlorite. Organic Letters, 2013, 15 (9), pp.2294-2297. ⟨10.1021/ol400865b⟩. ⟨hal-00997432⟩
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