An Effective Method for Allylic Oxidation of Δ5-Steroids Using tert-Butyl Hydroperoxide

被引：21

作者：

Li, Yuancheng ^{[1
]}

Wu, Xianhong ^{[1
]}

Lee, Tae Bum ^{[1
]}

Isbell, Eleanor K. ^{[1
]}

Parish, Edward J. ^{[1
]}

Gorden, Anne E. V. ^{[1
]}

机构：

[1] Auburn Univ, Dept Chem & Biochem, Coll Sci & Math, Auburn, AL 36849 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 75卷 / 05期

关键词：

DIRHODIUM CAPROLACTAMATE; OXYSTEROLS; 7-KETOCHOLESTEROL; LOCALIZATION; ALKENES; REAGENT;

D O I：

10.1021/jo902637k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An allylic oxidation method for Delta(5)-steroids using TBHP as oxidant with a 2-quinoxalinol salen Cu(II) complex as catalyst is reported. A variety of Delta(5)-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.

引用

页码：1807 / 1810

页数：4

共 33 条

[1] Allylic oxidation of steroidal olefins by vanadyl acetylacetonate and tert-butyl hydroperoxide
Grainger, Wendell S.
Parish, Edward J.
STEROIDS, 2015, 101 : 103 - 109
[2] N-Hydroxyphthalimide catalyzed allylic oxidation of steroids with t-butyl hydroperoxide
Zhao, Qian
Qian, Chao
Chen, Xin-Zhi
STEROIDS, 2015, 94 : 1 - 6
[3] Allylic C-H Activations Using Cu(II) 2-Quinoxalinol Salen and tert-Butyl Hydroperoxide
Li, Yuancheng
Lee, Tae Bum
Wang, Tanyu
Gamble, Audrey V.
Gorden, Anne E. V.
JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (10) : 4628 - 4633
[4] tert-Butyl Hydroperoxide-Mediated Synthesis of Phosphoroselenoates
Zhang Yunqian
Zhou Chenfan
Liu Gongqing
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2022, 42 (01) : 218 - 225
[5] Recyclable Dirhodium(II) Catalyst Rh2(esp)2 for the Allylic Oxidation of Δ5-Steroids
Wang, Yi
Kuang, Yi
Zhang, Hongyang
Ma, Ruocheng
Wang, Yuanhua
JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (09) : 4729 - 4736
[6] Catalytic Oxidative Cleavage Reactions of Arylalkenes by tert-Butyl Hydroperoxide - A Mechanistic Assessment
Su, Yong-Liang
De Angelis, Luca
Tram, Linh
Yu, Yang
Doyle, Michael P.
JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (05) : 3728 - 3741
[7] Epoxidation of electron deficient alkenes using tert-butyl hydroperoxide and 1,5,7-triazabicyclo[4.4.0]dec-5-ene and its derivatives
Genski, T
Macdonald, G
Wei, XD
Lewis, N
Taylor, RJK
SYNLETT, 1999, (06) : 795 - 797
[8] Polymer-supported Oxone and tert-butyl hydroperoxide: new reagents for the epoxidation of α,β-unsaturated aldehydes and ketones
Pourali, Ali Reza
MENDELEEV COMMUNICATIONS, 2010, 20 (02) : 113 - 115
[9] tert-Butyl Hydroperoxide (TBHP)-Initiated Vicinal Sulfonamination of Alkynes: A Radical Annulation toward 3-Sulfonylindoles
Chen, Fei
Meng, Qiang
Han, Shang-Qing
Han, Bing
ORGANIC LETTERS, 2016, 18 (14) : 3330 - 3333
[10] Catalytic activity of carbon nanotube supported iron(III) and manganese(III) porphyrins in oxidation of olefins with tert-butyl hydroperoxide: Higher activity of the iron(III) porphyrin
Rayati, Saeed
Jafarzadeh, Parisa
Zakavi, Saeed
INORGANIC CHEMISTRY COMMUNICATIONS, 2013, 29 : 40 - 44

← 1 2 3 4 →