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Highly enantioselective CH oxidation of vic-Diols with Shi's oxazolidinone dioxiranes.

ABSTRACT: [reaction: see text] Through an analogical study of the transition states of CH oxidation and asymmetric epoxidation of terminal alkenes, the first dioxirane-mediated catalytic highly enantioselective CH oxidation method was realized with Shi's oxazolidinone ketone derivatives. Very good enantioselectivity (up to 92% ee) may be obtained for both asymmetrization of meso vic-diols and kinetic resolution of racemic vic-diols.

SUBMITTER: Jakka K

PROVIDER: S-EPMC2593872 | biostudies-literature | 2006 Jul

REPOSITORIES: biostudies-literature

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Highly enantioselective CH oxidation of vic-Diols with Shi's oxazolidinone dioxiranes.

Jakka Kavitha K Zhao Cong-Gui CG

Organic letters 20060701 14

[reaction: see text] Through an analogical study of the transition states of CH oxidation and asymmetric epoxidation of terminal alkenes, the first dioxirane-mediated catalytic highly enantioselective CH oxidation method was realized with Shi's oxazolidinone ketone derivatives. Very good enantioselectivity (up to 92% ee) may be obtained for both asymmetrization of meso vic-diols and kinetic resolution of racemic vic-diols. ...[more]

PMID: 16805540

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