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

[31] MYERS RS, 1984, Patent No. 4496779
[32] Enantiospecific synthesis of (+)- and (-)-trachelanthic acids via asymmetric dihydroxylation and their conversion to the pyrrolizidine alkaloids indicine and intermedine
Nambu, M
White, JD
[J]. CHEMICAL COMMUNICATIONS, 1996, (14) : 1619 - 1620
[33] POHL G, 1985, ULLMANNS ENCY IND A, V1, P305
[34] OSMIUM-TETROXIDE CATALYZED HYDROXYLATION OF HINDERED OLEFINS
RAY, R
MATTESON, DS
[J]. TETRAHEDRON LETTERS, 1980, 21 (05) : 449 - 450
[35] Schneider W. P., 1956, U. S. Patent, Patent No. 2769824
[36] OSMIUM TETRAOXIDE CIS-HYDROXYLATION OF UNSATURATED SUBSTRATES
SCHRODER, M
[J]. CHEMICAL REVIEWS, 1980, 80 (02) : 187 - 213
[37] OSMIUM CATALYZED VICINAL HYDROXYLATION OF OLEFINS BY TERT-BUTYL HYDROPEROXIDE UNDER ALKALINE CONDITIONS
SHARPLESS, KB
AKASHI, K
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (07) : 1986 - 1987
[38] THE OSMIUM-CATALYZED ASYMMETRIC DIHYDROXYLATION - A NEW LIGAND CLASS AND A PROCESS IMPROVEMENT
SHARPLESS, KB
AMBERG, W
BENNANI, YL
CRISPINO, GA
HARTUNG, J
JEONG, KS
KWONG, HL
MORIKAWA, K
WANG, ZM
XU, DQ
ZHANG, XL
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (10) : 2768 - 2771
[39] SINGH MP, 1975, INDIAN J CHEM, V13, P112
[40] Total synthesis of goniocin and cyclogoniodenin T. Unique biosynthetic implications
Sinha, SC
Sinha, A
Sinha, SC
Keinan, E
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (16) : 4017 - 4018

← 1 2 3 4 5 →