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Efficient Synthesis of Unsymmetrical Disulfides through Sulfenic Acids
Author(s) -
Aversa Maria Chiara,
Barattucci Anna,
Bonaccorsi Paola
Publication year - 2009
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200900986
Subject(s) - sulfenic acid , chemistry , thermolabile , thiol , combinatorial chemistry , disulfide bond , organic chemistry , biochemistry , cysteine , enzyme
Abstract Unsymmetrical disulfides, some of which are biologically interesting, were prepared by the in situ generation of sulfenic acids from suitable sulfinyl precursors and their coupling with various thiols. This methodology represents an efficient and mild procedure to obtain disulfides in excellent yields. It allows the presence of base/acid and/or thermolabile functional groups in both the sulfenic acid and the thiol on the basis of the choice of suitable sulfenic acid precursors and offers wide chances of modulating the construction of the disulfide bridge between different structural skeletons such as homo‐ and heteroaromatic, amino acidic and sugar residues. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)