The effect of fluorine substitution at the 5, 5', 6, 6', 7, 7', 8 and 8' po
sitions of 2,2'-dihydroxy-1,1'-binaphthyl (BINOL) on its catalytic activity
in titanium-mediated sulfide oxidation with tert-butyl hydrogen peroxide a
nd cumyl hydrogen peroxide was examined. Introduction of fluorines into the
BINOL scaffold was found to increase the electrophilic character of the Le
wis acidic titanium center of the catalyst. Moreover, under otherwise ident
ical conditions, BINOL and 5,5',6,6',7,7',8,8'-octafluoro-2,2'-dihydroxy-1,
1'-binaphthyl (F8BINOL) of the same absolute configuration led to opposite
sense of chiral induction in the sulfoxidation process. (C) 2000 Published
by Elsevier Science S.A. All rights reserved.