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Letter

Catalyst-Free Conjugated Addition of Thiols to α,β-Unsaturated Carbonyl Compounds in Water

Supporting Info

Gopal L. Khatik, Raj Kumar, and Asit K. Chakraborti*

Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research (NIPER), Sector 67, S. A. S. Nagar, Punjab 160 062, India

Org. Lett., 2006, 8 (11), pp 2433–2436

DOI: 10.1021/ol060846t

Publication Date (Web): May 4, 2006

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, akchakraborti@niper.ac.in

Abstract

Catalyst-free conjugate addition of thiols to α,β-unsaturated carbonyl compounds in water is reported. β-Sulfido carbonyl compounds were formed at room temperature, in short times and with excellent chemoselectivity. Competitive dithiane/dithiolane formation, transesterification, and ester cleavage were not observed. Water played a dual role in simultaneously activating the α,β-unsaturated carbonyl compound and the thiol. This new methodology constitutes an easy, highly efficient, and green synthesis of β-sulfido carbonyl compounds.

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