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Synthesis of (Enantioenriched) Dibenzyl Thioethers and Disulfides via S N 2 Nucleophilic Substitution of Quaternary Ammonium Salts
Author(s) -
Tang Qinqin,
Li Fuhai,
Chen Hongyi,
Yin Xianjie,
Tang Yan,
Zeng Qingle
Publication year - 2021
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.202100269
Subject(s) - chemistry , ammonium , nucleophilic substitution , nucleophile , sulfide , quaternary , sodium sulfide , enantioselective synthesis , organic chemistry , medicinal chemistry , catalysis , paleontology , biology
A synthetic protocol of dibenzyl thioethers and dibenzyl disulfides via S N 2 nucleophilic substitution of quaternary ammonium salts and sodium sulfide nonahydrate and disodium disulfide under mild condition is described. In particular, if quaternary ammonium salts synthesized from enantiomerically enriched amines are adopted, highly enantioenriched dibenzyl thioethers (92–95% ee) with reverse configurations to their enantioenriched quaternary ammonium salts are obtained.