Oxidation of Silyl Enol Ethers Using 2-Sulfonyloxaziridines. Synthesis of α-Siloxy Epoxides and α-Hydroxy Carbonyl Compounds

DOI: 10.1021/jo00381a051

Source and publish data:

Journal of Organic Chemistry p. 954 - 955 (1987)

Update date:2022-08-05

Topics:

Authors:

Davis, Franklin A.

Sheppard, Aurelia C.

Read Full Text PDF DownLoad Join now for total 90,000,000 free articles

Article abstract of DOI:10.1021/jo00381a051

The first isolation and detection of α-siloxy epoxides 2 in the oxidation of silyl enol ethers 1 to α-hydroxy carbonyl compounds 4 (Rubottom reaction) by 2-sulfonyloxaziridine 5 is described.Asymmetric oxidation of silyl enol ethers by (+)-(R,R)-6 affords optically active α-hydroxy carbonyl compounds.

Full text of DOI:10.1021/jo00381a051

Products guided by the article

Product name:Silane, trimethyl[(3-methyl-2-phenyloxiranyl)oxy]-

Cas No:105597-91-9

R&D Labs maybe for 105597-91-9

Mollt Biochem Co., Ltd(expird)

Contact:+86-21-38682181

Address:shanghai ,china
Shijiazhuang Haotian Chemical Co., Ltd.

Contact:86-311-85044374

Address:293 Donggang Road
SHANGHAI RC CHEMICALS CO.,LTD.

website:http://www.rcc.net.cn

Contact:+86-21-50322175

Address:Rm1415 Yinqiao Masion No.58 Jinxin Road Pudong Shanghai China
Shanghai Surseechem Co.,Ltd.

Contact:+86-21-61318535

Address:Building 29,No.2139 Xizha Road, Fengxian District, Shanghai
Nanjing Norris Pharm Technology Co., Ltd.

Contact:+86-13901585132

Address:2 Qiande Road, Jiangning sciencepark Hi-Tech Zone, Nanjing, P.R.China

Relevant to this article

Lower rim 1,3-di{bis(2-picolyl)}amide derivative of calix[4]arene (L) as ratiometric primary sensor toward Ag⁺ and the complex of Ag ⁺ as secondary sensor toward cys: Experimental, computational, and microscopy studies and INHIBIT logic gate properties of L

Doi:10.1021/jo901676s
(2009)
2-Aminomethylphenylamine as a novel scaffold for factor Xa inhibitor

Doi:10.1016/j.bmc.2011.01.035
(2011)
Extended pummerer reaction of arylketene dithioacetal monoxides with aromatic compounds by means of trifluoromethanesulfonic anhydride

Doi:10.1246/cl.2008.786
(2008)
Asymmetric synthesis of 3,4-annulated cyclopentenones from cycloalkenyl ketones and vinyl carbamates by diastereoselective carbonyl addition/conrotatory 4π ring closure

Doi:10.1055/s-2008-1067150
(2008)
A NMR, X-ray, and DFT combined study on the regio-chemistry of nucleophilic addition to platinum(II) coordinated terminal olefins

Doi:10.1016/j.jorganchem.2008.05.040
(2008)
Synthesis of C₆₀-fused tetrahydrothiophene derivatives via nucleophilic cycloaddition of thiocyanates

Doi:10.1039/b807394e
(2008)

Article Doi