Diastereoselective epoxidation of cyclohexene derivatives by dioxiranes generated in situ. Importance of steric and field effects

Dan Yang; Guan Sheng Jiao; Yiu Chung Yip; Man Kin Wong

doi:10.1021/jo9821978

Diastereoselective epoxidation of cyclohexene derivatives by dioxiranes generated in situ. Importance of steric and field effects

Dan Yang, Guan Sheng Jiao, Yiu Chung Yip, Man Kin Wong

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

51 Citations (Scopus)

Abstract

In this paper, diastereoselective epoxidation of substituted cyclohexenes (substrates 1-7) by dioxiranes generated in situ from ketones and Oxone was systematically investigated. The results revealed that the diastereoselectivity was determined by the steric and field effects of both dioxiranes and substrates, and high diastereoselectivity can be achieved by tuning the ketone structure. Among the ketones tested, 12 and 19 gave the best diastereoselectivities.

Original language	English
Pages (from-to)	1635-1639
Number of pages	5
Journal	Journal of Organic Chemistry
Volume	64
Issue number	5
DOIs	https://doi.org/10.1021/jo9821978
Publication status	Published - 5 Mar 1999
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry

More information

10.1021/jo9821978

Cite this

@article{d72837de3fc148e3b2a6a486a272d917,

title = "Diastereoselective epoxidation of cyclohexene derivatives by dioxiranes generated in situ. Importance of steric and field effects",

abstract = "In this paper, diastereoselective epoxidation of substituted cyclohexenes (substrates 1-7) by dioxiranes generated in situ from ketones and Oxone was systematically investigated. The results revealed that the diastereoselectivity was determined by the steric and field effects of both dioxiranes and substrates, and high diastereoselectivity can be achieved by tuning the ketone structure. Among the ketones tested, 12 and 19 gave the best diastereoselectivities.",

author = "Dan Yang and Jiao, {Guan Sheng} and Yip, {Yiu Chung} and Wong, {Man Kin}",

year = "1999",

month = mar,

day = "5",

doi = "10.1021/jo9821978",

language = "English",

volume = "64",

pages = "1635--1639",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "5",

}

TY - JOUR

T1 - Diastereoselective epoxidation of cyclohexene derivatives by dioxiranes generated in situ. Importance of steric and field effects

AU - Yang, Dan

AU - Jiao, Guan Sheng

AU - Yip, Yiu Chung

AU - Wong, Man Kin

PY - 1999/3/5

Y1 - 1999/3/5

N2 - In this paper, diastereoselective epoxidation of substituted cyclohexenes (substrates 1-7) by dioxiranes generated in situ from ketones and Oxone was systematically investigated. The results revealed that the diastereoselectivity was determined by the steric and field effects of both dioxiranes and substrates, and high diastereoselectivity can be achieved by tuning the ketone structure. Among the ketones tested, 12 and 19 gave the best diastereoselectivities.

AB - In this paper, diastereoselective epoxidation of substituted cyclohexenes (substrates 1-7) by dioxiranes generated in situ from ketones and Oxone was systematically investigated. The results revealed that the diastereoselectivity was determined by the steric and field effects of both dioxiranes and substrates, and high diastereoselectivity can be achieved by tuning the ketone structure. Among the ketones tested, 12 and 19 gave the best diastereoselectivities.

UR - http://www.scopus.com/inward/record.url?scp=0033525675&partnerID=8YFLogxK

U2 - 10.1021/jo9821978

DO - 10.1021/jo9821978

M3 - Journal article

SN - 0022-3263

VL - 64

SP - 1635

EP - 1639

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 5

ER -

Diastereoselective epoxidation of cyclohexene derivatives by dioxiranes generated in situ. Importance of steric and field effects

Abstract

ASJC Scopus subject areas

More information

Other files and links

Fingerprint

Cite this