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
收藏
页码：6250 / 6253
页数：4
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