Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 349, Issue 3, Pages 357-363Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.200600267
Keywords
asymmetric oxidation; kinetic resolution; optically pure alkyl hydroperoxides; sulfoxides; titanium
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A functionalized tertiary furyl hydroperoxide derived from (S)-norcamphor has been easily synthesized in good yield and in a highly diastereoselective manner. Good to high enantioselectivities (up to 99 % ee) and acceptable to good yields (up to 86 %) were achieved for the sulfoxides, by tandem stereoconvergent asymmetric sulfoxidation and kinetic resolution when using the novel hydroperoxide as oxygen donor and chirality source in the presence of catalytic loadings of titanium(IV) isopropoxide as the catalyst.
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