A new practical method for the osmium-catalyzed dihydroxylation of olefins using bleach as the terminal oxidant

被引：0
作者：
Mehltretter, GM
Bhor, S
Klawonn, M
Döbler, C
Sundermeier, U
Eckert, M
Militzer, HC
Beller, M
机构：
[1] Univ Rostock eV, Inst Organ Katalyseforsch IfOK, D-18055 Rostock, Germany
[2] Bayer AG, D-51368 Leverkusen, Germany
来源：
SYNTHESIS-STUTTGART | 2003年 / 02期
关键词：
asymmetric catalysis; dihydroxylation; homogenous catalysis; osmium; oxidations;
D O I：
暂无
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A general procedure for the osmium-catalyzed dihydroxylation of various olefins using bleach as oxidant is reported for the first time. Aromatic and aliphatic olefins yield the corresponding cis-1,2-diols in the presence of dihydroquinine or dihydroquinidine derivatives (Sharpless ligands) with good to excellent chemo- and enantioselectivities under optimized pH conditions. In the presence of a small excess of bleach as reoxidant fast dihydroxylation takes place even at 0 degreesC. Under optimum reaction conditions it is possible to dihydroxylate terminal aliphatic and aromatic olefins as well as internal olefins. The low price of the oxidant and the simple handling of bleach make this dihydroxylation variant attractive for further applications.
引用
收藏
页码：295 / 301
页数：7
相关论文
共 49 条
[1]  
Andersson MA, 2002, ANGEW CHEM INT EDIT, V41, P472, DOI 10.1002/1521-3773(20020201)41:3<472::AID-ANIE472>3.0.CO
[2]  
2-7
[3]  
[Anonymous], 1994, CHEM ENG NEWS, V72, P41
[4]  
Beller M, 2001, CHEM ENG TECHNOL, V24, P575, DOI 10.1002/1521-4125(200106)24:6<575::AID-CEAT575>3.0.CO
[5]  
2-D
[6]  
BELLER M, 1996, APPL HOMOGENEOUS CAT, P1009
[7]   A new coupled catalytic system for dihydroxylation of olefins by H2O2 [J].
Bergstad, K ;
Jonsson, SY ;
Bäckvall, JE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (44) :10424-10425
[8]   LIGAND-ACCELERATED CATALYSIS [J].
BERRISFORD, DJ ;
BOLM, C ;
SHARPLESS, KB .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (10) :1059-1070
[9]  
Bolm C., 2000, Catal. Asymmetric Synth, V2nd, P399
[10]   SHORT ENANTIOSELECTIVE SYNTHESIS OF (-)-OVALICIN, A POTENT INHIBITOR OF ANGIOGENESIS, USING SUBSTRATE-ENHANCED CATALYTIC ASYMMETRIC DIHYDROXYLATION [J].
COREY, EJ ;
GUZMANPEREZ, A ;
NOE, MC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (26) :12109-12110
12345