Ionic liquid [Hmim]HSO4-promoted one-pot oxidative conjugate addition of sulfur-centred nucleophiles to Baylis–Hillman adducts
- 作者：Lal Dhar S. Yadav ; Vishnu P. Srivastava ; Rajesh Patel
- 关键词：Baylis– ; Hillman adducts ; Conjugate addition ; Oxidation ; Ionic liquids ; Cinnamaldehydes ; Stereoselective synthesis
- 刊名：Tetrahedron Letters
- 出版年：2008
- 期刊代码：109_00404039
- 类别：ch
- 出版时间：5 May 2008
- 卷：49
- 期：19
- 页码：3142-3146
- 文件大小：141 K
摘要
The first example of the one-pot oxidative conjugate addition of sulfur-centred nucleophiles to Baylis–Hillman adducts is reported. The reaction involves oxidation of Baylis–Hillman adducts with NaNO3 in the Brønsted acidic ionic liquid [Hmim]HSO4 to give [E]-
-cyanocinnamaldehydes followed by conjugate hydrothiocyanation/hydrosulfenylation with NH4SCN/PhSH to afford the corresponding β-thiocyanato (or β-phenylsulfenyl)--cyanohydrocinnamaldehydes diastereoselectively in 76–89%yields in a one-pot procedure. After isolation of the product, the ionic liquid [Hmim]HSO4 could be easily recycled for further use.
-cyanocinnamaldehydes followed by conjugate hydrothiocyanation/hydrosulfenylation with NH4SCN/PhSH to afford the corresponding β-thiocyanato (or β-phenylsulfenyl)--cyanohydrocinnamaldehydes diastereoselectively in 76–89%yields in a one-pot procedure. After isolation of the product, the ionic liquid [Hmim]HSO4 could be easily recycled for further use.