Journal
TETRAHEDRON
Volume 66, Issue 13, Pages 2297-2300Publisher
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
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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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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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