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Enantioselective Sulfide Oxidation Catalyzed by 2,10‐Camphanediol Derived Titanium Complex and Its Mechanism
Author(s) -
ZENG QingLe,
TANG HongYan,
ZHANG Song,
LIU JianChuan
Publication year - 2008
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.200890261
Subject(s) - chemistry , sulfoxide , sulfide , enantioselective synthesis , intramolecular force , catalysis , kinetic resolution , nucleophile , titanium , mechanism (biology) , medicinal chemistry , combinatorial chemistry , organic chemistry , philosophy , epistemology
Cumyl hydroperoxide (CHP) and tert ‐butyl hydroperoxide (TBHP) produced ( R )‐ and ( S )‐sulfoxide in 2,10‐camphanediol‐titanium catalyzed sulfoxidation, respectively. During kinetic resolution, the sulfoxide configuration was reversed with CHP, but kept with TBHP. Based on these results and the ESI‐MS data, the mechanism of sulfoxidation was proposed to be intramolecular nucleophilic oxygen transfer to a coordinated sulfide.