An effective method for allylic oxidation of Delta-5-steroids using tert-butyl hydroperoxide

Yuancheng Li; Xianghong Wu; Tae Bum Lee; Eleanor K Isbell; Edward J Parish; Anne Gorden

doi:10.1021/jo902637k

An effective method for allylic oxidation of Delta-5-steroids using tert-butyl hydroperoxide

Yuancheng Li, Xianghong Wu, Tae Bum Lee, Eleanor K Isbell, Edward J Parish, Anne Gorden

Chemistry and Biochemistry

Research output: Contribution to journal › Article › peer-review

Abstract

An allylic oxidation method for Δ⁵-steroids using TBHP as oxidant with a 2-quinoxalinol salen Cu(II) complex as catalyst is reported. A variety of Δ⁵-steroidal substrates are selectively oxidized to the corresponding enones. Excellent yields are achieved (up to 99% under optimized conditions) while significantly reducing reaction times required as compared to other current methods.

Original language	English
Pages (from-to)	1807--1810
Journal	Journal of Organic Chemistry
DOIs	https://doi.org/10.1021/jo902637k
State	Published - 2010

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@article{1764e5fb238e4800ba874a65edfc85b6,

title = "An effective method for allylic oxidation of Delta-5-steroids using tert-butyl hydroperoxide",

abstract = "An allylic oxidation method for Δ5-steroids using TBHP as oxidant with a 2-quinoxalinol salen Cu(II) complex as catalyst is reported. A variety of Δ5-steroidal substrates are selectively oxidized to the corresponding enones. Excellent yields are achieved (up to 99% under optimized conditions) while significantly reducing reaction times required as compared to other current methods.",

author = "Yuancheng Li and Xianghong Wu and Lee, {Tae Bum} and Isbell, {Eleanor K} and Parish, {Edward J} and Anne Gorden",

year = "2010",

doi = "10.1021/jo902637k",

language = "English",

pages = "1807----1810",

journal = "Journal of Organic Chemistry",

publisher = "American Chemical Society",

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T1 - An effective method for allylic oxidation of Delta-5-steroids using tert-butyl hydroperoxide

AU - Li, Yuancheng

AU - Wu, Xianghong

AU - Lee, Tae Bum

AU - Isbell, Eleanor K

AU - Parish, Edward J

AU - Gorden, Anne

PY - 2010

Y1 - 2010

N2 - An allylic oxidation method for Δ5-steroids using TBHP as oxidant with a 2-quinoxalinol salen Cu(II) complex as catalyst is reported. A variety of Δ5-steroidal substrates are selectively oxidized to the corresponding enones. Excellent yields are achieved (up to 99% under optimized conditions) while significantly reducing reaction times required as compared to other current methods.

AB - An allylic oxidation method for Δ5-steroids using TBHP as oxidant with a 2-quinoxalinol salen Cu(II) complex as catalyst is reported. A variety of Δ5-steroidal substrates are selectively oxidized to the corresponding enones. Excellent yields are achieved (up to 99% under optimized conditions) while significantly reducing reaction times required as compared to other current methods.

U2 - 10.1021/jo902637k

DO - 10.1021/jo902637k

M3 - Article

SP - 1807

EP - 1810

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

ER -

An effective method for allylic oxidation of Delta-5-steroids using tert-butyl hydroperoxide

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