Dihydroxylation of olefins using air as the terminal oxidant

被引：58

作者：

Döbler, C ^{[1
]}

Mehltretter, GM ^{[1
]}

Sundermeier, U ^{[1
]}

Beller, M ^{[1
]}

机构：

[1] Univ Rostock, IfOK, D-18055 Rostock, Germany

来源：

JOURNAL OF ORGANOMETALLIC CHEMISTRY | 2001年 / 621卷 / 1-2期

关键词：

oxidation; asymmetric dihydroxylation; osmium; air;

D O I：

10.1016/S0022-328X(00)00856-1

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A study of the osmium-catalyzed dihydroxylation of various olefins using air as the stoichiometric oxidant is described. Dihydroxylation takes place smoothly at an air pressure of 20 bar, at 50 degreesC and pH 10.4. in the presence of dihydroquinine or dihydroquinidine derivatives (Sharpless ligands) asymmetric dihydroxylations occur with only slightly lower enantioselectivities compared to the classical K-3[Fe(CN)(6)] reoxidation system. In the case of stilbene the solvent system is crucial in determining the chemoselectivity of the reaction. The first example of a selective metal catalyzed oxidative cleavage of an olefin with air to give aldehydes is presented. (C) 2001 Elsevier Science B.V. All rights reserved.

引用

页码：70 / 76

页数：7

共 47 条

[1] Absolute configuration of α-methylstyrene oxide:: The correct absolute configuration/optical rotation correlation
Archelas, A
Furstoss, R
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (16) : 6112 - 6114
[2] BELLER M, 1996, APPL HOMOGENEOUS CAT, P1009
[3] BELLER M, 1998, TRANSITION METALS OR
[4] A SHORT ROUTE TO A MOSHERS ACID PRECURSOR VIA CATALYTIC ASYMMETRIC DIHYDROXYLATION (AD)
BENNANI, YL
VANHESSCHE, KPM
SHARPLESS, KB
[J]. TETRAHEDRON-ASYMMETRY, 1994, 5 (08) : 1473 - 1476
[5] A new coupled catalytic system for dihydroxylation of olefins by H2O2
Bergstad, K
Jonsson, SY
Bäckvall, JE
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (44) : 10424 - 10425
[6] CAIRNS JF, 1966, Patent No. 1028940
[7] CAIRNS JF, 1996, J CHEM SOC C, P40
[8] SHORT ENANTIOSELECTIVE SYNTHESIS OF (-)-OVALICIN, A POTENT INHIBITOR OF ANGIOGENESIS, USING SUBSTRATE-ENHANCED CATALYTIC ASYMMETRIC DIHYDROXYLATION
COREY, EJ
GUZMANPEREZ, A
NOE, MC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (26) : 12109 - 12110
[9] THE APPLICATION OF A MECHANISTIC MODEL LEADS TO THE EXTENSION OF THE SHARPLESS ASYMMETRIC DIHYDROXYLATION TO ALLYLIC 4-METHOXYBENZOATES AND CONFORMATIONALLY RELATED AMINE AND HOMOALLYLIC ALCOHOL DERIVATIVES
COREY, EJ
GUZMANPEREZ, A
NOE, MC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (44) : 10805 - 10816
[10] Improved enantioselective dihydroxylation of bishomoallylic alcohol derivatives using a mechanistically inspired bis-cinchona alkaloid catalyst
Corey, EJ
Noe, MC
Ting, AY
[J]. TETRAHEDRON LETTERS, 1996, 37 (11) : 1735 - 1738

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