Khatik Gopal L, Kumar Raj, Chakraborti Asit K
Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research (NIPER), Punjab, India.
Org Lett. 2006 May 25;8(11):2433-6. doi: 10.1021/ol060846t.
[reaction: see text] Catalyst-free conjugate addition of thiols to alpha,beta-unsaturated carbonyl compounds in water is reported. beta-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 alpha,beta-unsaturated carbonyl compound and the thiol. This new methodology constitutes an easy, highly efficient, and green synthesis of beta-sulfido carbonyl compounds.
[反应：见正文] 据报道，在水中硫醇与α,β-不饱和羰基化合物可进行无催化剂的共轭加成反应。β-硫代羰基化合物在室温下短时间内即可形成，且具有出色的化学选择性。未观察到竞争性的二硫烷/二硫杂环戊烷形成、酯交换和酯裂解反应。水在同时活化α,β-不饱和羰基化合物和硫醇方面发挥了双重作用。这种新方法构成了一种简便、高效且绿色的β-硫代羰基化合物合成方法。
