☆ 4.4 Article

Rongalite® and base-promoted cleavage of disulfides and subsequent Michael addition to α,β-unsaturated ketones/esters: an odorless synthesis of β-sulfido carbonyl compounds

TETRAHEDRON (2010)

Journal

TETRAHEDRON

Volume 66, Issue 13, Pages 2297-2300

Publisher

PERGAMON-ELSEVIER SCIENCE LTD

DOI: 10.1016/j.tet.2010.02.001

Keywords

Rongalite (R); Thia-Michael addition; Disulfides; alpha,beta-Unsaturated ketones; alpha,beta-Unsaturated esters; beta-Sulfido carbonyl compounds

Categories

Chemistry, Organic

Funding

National Key Technology RD Program [2007BAI34B00]
National Natural Science Foundation of China [20471043]
Natural Science Foundation of Zhejiang Province [Y4080107]

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Abstract

A highly practical method to access beta-sulfido carbonyl compounds was developed, which could be conducted without any expensive reagent, special apparatus/technique, and no requirement of metal catalysts. beta-Sulfido carbonyl compounds were formed at room temperature, in short time and with high chemoselectivity in good to excellent yields. A plausible mechanism for the role of Rongalite (R), as a promoter for the cleavage of disuffides generating thiolate anions that then undergo facile thia-Michael addition to alpha,beta-unsaturated ketones and esters is proposed. (C) 2010 Elsevier Ltd. All rights reserved.

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