Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2021, Issue 41, Pages 5605-5608Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.202101086
Keywords
Chiral quaternary ammonium salts; C-Se bond formation; Chiral synthesis; Dibenzylic diselenides; Nucleophilic substitution
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In this study, substituted dibenzyl diselenides were synthesized in good yields (74-91%) through S(N)2 nucleophilic substitution of benzylic trimethylammonium salts and diselenide dianion (Se2-) under basic conditions. Highly enantiopure dibenzylic diselenides (95-98% ee) with reverse configurations to their enantioenriched quaternary ammonium salts are obtained when benzylic quaternary ammonium salts, synthesized from enantiomerically enriched amines, are used.
Abstract: Substituted dibenzyl diselenides are synthesized in good yields (74-91 %) by S(N)2 nucleophilic substitution of benzylic trimethylammonium salts and diselenide dianion (Se2-), in situ generated from elemental selenium, under basic conditions. Highly enantiopure dibenzylic diselenides (95-98 % ee) with reverse configurations to their enantioenriched quaternary ammonium salts are obtained, if benzylic quaternary ammonium salts, synthesized from enantiomerically enriched amines, are used.
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