An improved version of the Sharpless asymmetric dihydroxylation

被引：45

作者：

Mehltretter, GM ^{[1
]}

Döbler, C ^{[1
]}

Sundermeier, U ^{[1
]}

Beller, M ^{[1
]}

机构：

[1] Univ Rostock EV, Inst Organ Katalyseforsch, D-18055 Rostock, Germany

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 42期

关键词：

asymmetric dihydroxylations; olefins; osmium;

D O I：

10.1016/S0040-4039(00)01396-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The osmium catalyzed asymmetric dihydroxylation of olefins (Sharpless AD) was studied under controlled pH conditions. It was found that providing a constant pH value of 12.0 leads to improved reaction rates for internal olefins. Hydrolysis aids such as methanesulfonamide can be omitted. For terminal olefins, working at a constant pH of 10.0 at room temperature leads to higher enantioselectivities compared to AD reactions without pH control. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：8083 / 8087

页数：5

共 10 条

[1] MAJOR IMPROVEMENT IN OSMIUM CATALYZED VICINAL HYDROXYLATION OF OLEFINS BY TERT-BUTYL HYDROPEROXIDE [J].

AKASHI, K ;

PALERMO, RE ;

SHARPLESS, KB .

JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (10) :2063-2066

[2]

Döbler C, 1999, ANGEW CHEM INT EDIT, V38, P3026

[3]

DOBLER C, IN PRESS J AM CHEM S

[4] CATALYTIC ASYMMETRIC DIHYDROXYLATION [J].

KOLB, HC ;

VANNIEUWENHZE, MS ;

SHARPLESS, KB .

CHEMICAL REVIEWS, 1994, 94 (08) :2483-2547

[5] SHORT AND PRACTICAL SYNTHESIS OF (R)-(-)-CARNITINE AND (R)-(-)-GAMMA-AMINO-BETA-HYDROXYBUTYRIC ACID (GABOB) [J].

KOLB, HC ;

BENNANI, YL ;

SHARPLESS, KB .

TETRAHEDRON-ASYMMETRY, 1993, 4 (01) :133-141

[6]

KOLB HC, 1998, TRANSITION METALS OR, V2, P219

[7]

Marko I. E., 1999, COMPREHENSIVE ASYMME, VII, P713

[8] CATALYTIC ASYMMETRIC DIHYDROXYLATION OF TETRASUBSTITUTED OLEFINS [J].

MORIKAWA, K ;

PARK, J ;

ANDERSSON, PG ;

HASHIYAMA, T ;

SHARPLESS, KB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (18) :8463-8464

[9] THE OSMIUM-CATALYZED ASYMMETRIC DIHYDROXYLATION - A NEW LIGAND CLASS AND A PROCESS IMPROVEMENT [J].

SHARPLESS, KB ;

AMBERG, W ;

BENNANI, YL ;

CRISPINO, GA ;

HARTUNG, J ;

JEONG, KS ;

KWONG, HL ;

MORIKAWA, K ;

WANG, ZM ;

XU, DQ ;

ZHANG, XL .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (10) :2768-2771

[10] ASYMMETRIC DIHYDROXYLATION OF PRIMARY ALLYLIC HALIDES AND A CONCISE SYNTHESIS OF (-)-DIEPOXYBUTANE [J].

VANHESSCHE, KPM ;

WANG, ZM ;

SHARPLESS, KB .

TETRAHEDRON LETTERS, 1994, 35 (21) :3469-3472

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