Alkene Dihydroxylation with Malonoyl Peroxides: Catalysis Using Fluorinated Alcohols

被引：52

作者：

Picon, Sylvain ^{[2
]}

Rawling, Michael ^{[1
]}

Campbell, Matthew ^{[3
]}

Tomkinson, Nicholas C. O. ^{[1
]}

机构：

[1] Univ Strathclyde, WestCHEM, Dept Pure & Appl Chem, Thomas Graham Bldg,295 Cathedral St, Glasgow G1 1XL, Lanark, Scotland

[2] Cardiff Univ, Sch Chem, Cardiff CF10 3AT, S Glam, Wales

[3] GlaxoSmithKline Med Res Ctr, Stevenage SG1 2NY, Herts, England

来源：

ORGANIC LETTERS | 2012年 / 14卷 / 24期

基金：

英国工程与自然科学研究理事会;

关键词：

NONHEME IRON CATALYSTS; METAL-FREE; AEROBIC DIOXYGENATION; CIS-DIHYDROXYLATION; DIMETHYL-SULFOXIDE; DIACETOXYLATION; PALLADIUM; ACIDITIES;

D O I：

10.1021/ol3030154

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The effect of fluorinated alcohols on the dihydroxylation of alkenes using cyclopropyl malonoyl peroxide is described. Addition of perfluoro-tert-butyl alcohol to a toluene solution of alkene and peroxide increases the rate of product formation and the stereoselectivity observed, providing a simple and effective method for acceleration of this important class of reaction. Basic hydrolysis of the crude reaction mixture provides access to syn-diols in high yield and stereoselectivity.

引用

页码：6250 / 6253

页数：4

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