期刊
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
卷 2006, 期 3, 页码 713-718出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.200500680
关键词
optically pure alkyl hydroperoxides; sulfoxidation; asymmetric synthesis; kinetic resolution; (S)-norcamphor
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, high chemoselectivity and improved asymmetric induction were achieved. The synthetic approach used offers the opportunity for designing a variety of functionalized and potentially more efficient norcamphor-based hydroperoxides. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006).
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