Zhang Qiaoling, Feng Hang, Chen Feng, He Ze, Zeng Qingle
State Key Laboratory of Geohazard Prevention and Geoenvironment Protection, College of Materials, Chemistry & Chemical Engineering, Chengdu University of Technology, Chengdu 610059, China.
J Org Chem. 2021 Jun 4;86(11):7806-7812. doi: 10.1021/acs.joc.1c00615. Epub 2021 May 17.
A KOH-promoted unusual deoxidative coupling reaction of β-sulfinyl esters with benzylic trimethylammonium salts to produce thioethers is discovered for the first time. If quaternary ammonium salts synthesized from enantiomerically enriched amines are adopted, highly enantiomerically enriched benzyl thioethers (>95-99% ee) with configurations opposite to those of the enantiomerically enriched amines are obtained.
首次发现了一种由氢氧化钾促进的β-亚磺酰基酯与苄基三甲基铵盐的异常脱氧偶联反应,用于制备硫醚。如果采用由对映体富集的胺合成的季铵盐,则可得到对映体高度富集的苄基硫醚(对映体过量>95-99%),其构型与对映体富集的胺相反。