Design and Synthesis of Chiral Ketones for Catalytic Asymmetric Epoxidation of Unfunctionalized Olefins

A series of C 2 symmetric chiral ketones were designed and synthesized for catalytic asymmetric epoxidation of unfunctionalized olefins. Among those ketones screened, (R)-7, (R)-9, and (R)-10 were found to be highly efficient catalysts for epoxidation of trans-stilbenes with enantioselectivities in...

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Bibliographic Details
Published in:Journal of the American Chemical Society 1998-06, Vol.120 (24), p.5943-5952
Main Authors: Yang, Dan, Wong, Man-Kin, Yip, Yiu-Chung, Wang, Xue-Chao, Tang, Man-Wai, Zheng, Jian-Hua, Cheung, Kung-Kai
Format: Article
Language:English
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Summary:A series of C 2 symmetric chiral ketones were designed and synthesized for catalytic asymmetric epoxidation of unfunctionalized olefins. Among those ketones screened, (R)-7, (R)-9, and (R)-10 were found to be highly efficient catalysts for epoxidation of trans-stilbenes with enantioselectivities in the range of 84−95%. Convincing evidence was provided for a spiro transition state of dioxirane epoxidation. Through the 18O-labeling experiment, chiral dioxiranes were found to be the intermediates in chiral ketone catalyzed epoxidation reactions.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja980428m