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.
The renewable tertiary (S)-norcamphor-based hydroperoxide 3 has been efficiently obtained by a simple 4-step route. Remarkably, complete diastereocontrol was observed in the hydroperoxidation step. This oxidant, when used in the Ti-catalyzed asymmetric sulfoxidation, showed to be as reactive as previously reported hydroperoxide 2, but more importantly,
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ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.
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