MODIFIED CINCHONA ALKALOID LIGANDS - IMPROVED SELECTIVITIES IN THE OSMIUM-TETROXIDE CATALYZED ASYMMETRIC DIHYDROXYLATION (AD) OF TERMINAL OLEFINS

被引：26

作者：

ARRINGTON, MP ^{[1
]}

BENNANI, YL ^{[1
]}

GOBEL, T ^{[1
]}

WALSH, P ^{[1
]}

ZHAO, SH ^{[1
]}

SHARPLESS, KB ^{[1
]}

机构：

[1] Scripps Res Inst, DEPT CHEM, 10666 N TORREY PINES RD, LA JOLLA, CA 92037 USA

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 46期

基金：

美国国家卫生研究院;

关键词：

D O I：

10.1016/S0040-4039(00)60129-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Modification on the quinuclidine and the quinoline moieties of the bis cinchona-alkaloid phthalazine ligands resulted in improved enantioselectivities in the osmium tetroxide catalyzed dihydroxylation of olefins. For the first time 1-decene, a common model for terminal aliphatic olefins, afforded enantioselectivities of over ninety percent.

引用

页码：7375 / 7378

页数：4

共 8 条

[1] SYNTHESES AND CRYSTAL-STRUCTURES OF THE CINCHONA ALKALOID DERIVATIVES USED AS LIGANDS IN THE OSMIUM-CATALYZED ASYMMETRIC DIHYDROXYLATION OF OLEFINS
AMBERG, W
BENNANI, YL
CHADHA, RK
CRISPINO, GA
DAVIS, WD
HARTUNG, J
JEONG, KS
OGINO, Y
SHIBATA, T
SHARPLESS, KB
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (04) : 844 - 849
[2] BENNANI YL, UNPUB
[3] CRISPINO GA, IN PRESS J ORG CHEM
[4] HENTGES SG, 1980, J AM CHEM SOC, V102, P4263, DOI 10.1021/ja00532a050
[5] KOLB HC, UNPUB
[6] NEW LIGANDS DOUBLE THE SCOPE OF THE CATALYTIC ASYMMETRIC DIHYDROXYLATION OF OLEFINS
SHARPLESS, KB
AMBERG, W
BELLER, M
CHEN, H
HARTUNG, J
KAWANAMI, Y
LUBBEN, D
MANOURY, E
OGINO, Y
SHIBATA, T
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[J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (15) : 4585 - 4588
[7] 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
[8] ON THE STRUCTURE OF OSMIUM TETRAOXIDE CINCHONA ALKALOID COMPLEXES
SVENDSEN, JS
MARKO, I
JACOBSEN, EN
RAO, CP
BOTT, S
SHARPLESS, KB
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (10) : 2263 - 2264

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