Design and synthesis of chiral ketones for catalytic asymmetric epoxidation of unfunctionalized olefins

Dan Yang; Man Kin Wong; Yiu Chung Yip; Xue Chao Wang; Man Wai Tang; Jian Hua Zheng; Kung Kai Cheung

doi:10.1021/ja980428m

Design and synthesis of chiral ketones for catalytic asymmetric epoxidation of unfunctionalized olefins

Dan Yang, Man Kin Wong, Yiu Chung Yip, Xue Chao Wang, Man Wai Tang, Jian Hua Zheng, Kung Kai Cheung

Research output: Journal article publication › Journal article › Academic research › peer-review

186 Citations (Scopus)

Abstract

A series of C₂ 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.

Original language	English
Pages (from-to)	5943-5952
Number of pages	10
Journal	Journal of the American Chemical Society
Volume	120
Issue number	24
DOIs	https://doi.org/10.1021/ja980428m
Publication status	Published - 24 Jun 1998

ASJC Scopus subject areas

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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10.1021/ja980428m

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title = "Design and synthesis of chiral ketones for catalytic asymmetric epoxidation of unfunctionalized olefins",

abstract = "A series of C2 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.",

author = "Dan Yang and Wong, {Man Kin} and Yip, {Yiu Chung} and Wang, {Xue Chao} and Tang, {Man Wai} and Zheng, {Jian Hua} and Cheung, {Kung Kai}",

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T1 - Design and synthesis of chiral ketones for catalytic asymmetric epoxidation of unfunctionalized olefins

AU - Yang, Dan

AU - Wong, Man Kin

AU - Yip, Yiu Chung

AU - Wang, Xue Chao

AU - Tang, Man Wai

AU - Zheng, Jian Hua

AU - Cheung, Kung Kai

PY - 1998/6/24

Y1 - 1998/6/24

N2 - A series of C2 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.

AB - A series of C2 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.

UR - http://www.scopus.com/inward/record.url?scp=0031749334&partnerID=8YFLogxK

U2 - 10.1021/ja980428m

DO - 10.1021/ja980428m

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AN - SCOPUS:0031749334

SN - 0002-7863

VL - 120

SP - 5943

EP - 5952

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 24

ER -

Design and synthesis of chiral ketones for catalytic asymmetric epoxidation of unfunctionalized olefins

Abstract

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