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Asymmetric epoxidation of 1,1-disubstituted terminal olefins by chiral dioxirane via a planar-like transition state.

ABSTRACT: Various 1,1-disubstituted terminal olefins have been investigated for asymmetric epoxidation using chiral ketone catalysts. Up to 88% ee has been achieved with a lactam ketone, and a planar transition state is likely to be a major reaction pathway.

SUBMITTER: Wang B

PROVIDER: S-EPMC2736380 | biostudies-literature | 2008 Dec

REPOSITORIES: biostudies-literature

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Asymmetric epoxidation of 1,1-disubstituted terminal olefins by chiral dioxirane via a planar-like transition state.

Wang Bin B Wong O Andrea OA Zhao Mei-Xin MX Shi Yian Y

The Journal of organic chemistry 20081201 24

Various 1,1-disubstituted terminal olefins have been investigated for asymmetric epoxidation using chiral ketone catalysts. Up to 88% ee has been achieved with a lactam ketone, and a planar transition state is likely to be a major reaction pathway. ...[more]

PMID: 18850744

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