Osmium-free direct syn-dihydroxylation of alkenes

被引：199
作者：
Bataille, Carole J. R. [1 ]
Donohoe, Timothy J. [1 ]
机构：
[1] Univ Oxford, Dept Chem, Chem Res Lab, Oxford OX1 3TA, England
来源：
CHEMICAL SOCIETY REVIEWS | 2011年 / 40卷 / 01期
关键词：
OLEFIN CIS-DIHYDROXYLATION; DIOXYGENASE-CATALYZED DIHYDROXYLATION; NONHEME IRON CATALYSTS; PERMANGANATE OXIDATION; UNSATURATED-COMPOUNDS; STEREOSELECTIVE DIHYDROXYLATION; ASYMMETRIC DIHYDROXYLATION; VICINAL HYDROXYLATION; EFFICIENT SYNTHESIS; DL-PROTO;
D O I：
10.1039/b923880h
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Numerous synthetic protocols for producing syn-diols from the corresponding alkenes have been developed and published over recent years. It is the intent of the following tutorial review to present a concise summary of the main methods used to prepare syn-diol fragments directly from alkene precursors, and that do not make use of osmium oxo complexes as catalysts.
引用
收藏
页码：114 / 128
页数：15
相关论文
共 106 条
[1]   MICROBIOLOGICAL PREPARATION OF (S)-(+)-2,3-DIHYDROXY-3-METHYLBUTANOIC ACID BY SYN DIHYDROXYLATION OF 3-METHYLCROTONIC ACID [J].
ABERHART, DJ .
JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (25) :5218-5220
[2]   DOUBLE ASYMMETRIC INDUCTION IN THE OSMYLATION OF GAMMA-ALKOXY-ALPHA,BETA-UNSATURATED ESTERS [J].
ANNUNZIATA, R ;
CINQUINI, M ;
COZZI, F ;
RAIMONDI, L .
TETRAHEDRON, 1988, 44 (22) :6897-6902
[3]  
[Anonymous], 1881, BER DTSCH CHEM GES
[4]   SIMPLE METHODS OF CIS-HYDROXYLATION OF F-ALKYLETHYLENES [J].
AYARI, A ;
SZONYI, S ;
ROUVIER, E ;
CAMBON, A .
JOURNAL OF FLUORINE CHEMISTRY, 1990, 50 (01) :67-75
[5]  
Backvall J.-E., 2010, MODERN OXIDATION MET
[6]   Stereochemistry of dihydroxylation of N-arylbicyclo[2.2.1]-hept-5-ene-endo- and -exo-2,3-dicarboximides [J].
Bagmanov, B. T. .
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 43 (11) :1635-1641
[7]   cis-dihydroxylation of alkenes by a non-heme iron enzyme mimic [J].
Barry, Sarah M. ;
Rutledge, Peter J. .
SYNLETT, 2008, (14) :2172-2174
[8]   Biomimetic high-valent non-heme iron oxidants for the cis-dihydroxylation and epoxidation of olefins [J].
Bautz, Jochen ;
Comba, Peter ;
de laorden, Carlos Lopez ;
Menzel, Matthias ;
Rajaraman, Gopalan .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (42) :8067-8070
[9]   Sequential catalysis: A metathesis/dihydroxylation sequence [J].
Beligny, S ;
Eibauer, S ;
Maechling, S ;
Blechert, S .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (12) :1900-1903
[10]  
Beller M., 2000, WO Pat., Patent No. [W2000064848, 2000064848]
12345678910