Asymmetric catalysis by a chiral ruthenium porphyrin: Epoxidation, hydroxylation, and partial kinetic resolution of hydrocarbons

被引：110

作者：

Gross, Z ^{[1
]}

Ini, S

机构：

[1] Technion Israel Inst Technol, Dept Chem, IL-32000 Haifa, Israel

[2] Technion Israel Inst Technol, Inst Catalysis Sci & Technol, IL-32000 Haifa, Israel

来源：

ORGANIC LETTERS | 1999年 / 1卷 / 13期

关键词：

D O I：

10.1021/ol991131b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A new member of our D-2 symmetry ruthenium porphyrins is shown to be a most selective catalyst for asymmetric epoxidation of terminal and trans-disubstituted olefins. The same catalyst displays some selectivity in kinetic resolution of secondary alcohols and in what appears to be the first example of catalytic enantioselective hydroxylation of tertiary alkanes.

引用

页码：2077 / 2080

页数：4

共 24 条

[1] Catalytic asymmetric epoxidation with a chiral ruthenium porphyrin and N-oxides
Berkessel, A
Frauenkron, M
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (16): : 2265 - 2266
[2] THREITOL-STRAPPED MANGANESE PORPHYRINS AS ENANTIOSELECTIVE EPOXIDATION CATALYSTS OF UNFUNCTIONALIZED OLEFINS
COLLMAN, JP
LEE, VJ
KELLENYUEN, CJ
ZHANG, XM
IBERS, JA
BRAUMAN, JI
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (02) : 692 - 703
[3] REGIOSELECTIVE AND ENANTIOSELECTIVE EPOXIDATION CATALYZED BY METALLOPORPHYRINS
COLLMAN, JP
ZHANG, XM
LEE, VJ
UFFELMAN, ES
BRAUMAN, JI
[J]. SCIENCE, 1993, 261 (5127) : 1404 - 1411
[4] An efficient catalyst for asymmetric epoxidation of terminal olefins
Collman, JP
Wang, Z
Straumanis, A
Quelquejeu, M
Rose, E
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (02) : 460 - 461
[5] End N, 1998, CHEM-EUR J, V4, P818, DOI 10.1002/(SICI)1521-3765(19980515)4:5<818::AID-CHEM818>3.0.CO
[6] 2-#
[7] A novel chiral ruthenium porphyrin as highly efficient and selective catalyst for asymmetric cyclopropanations
Frauenkron, M
Berkessel, A
[J]. TETRAHEDRON LETTERS, 1997, 38 (41) : 7175 - 7176
[8] Asymmetric cyclopropanation of alkenes and diazocarbonyl insertion into S-H bonds catalyzed by a chiral porphyrin Ru(II) complex.
Galardon, E
Roué, S
Le Maux, P
Simonneaux, G
[J]. TETRAHEDRON LETTERS, 1998, 39 (16) : 2333 - 2334
[9] Cyclopropanation of alkenes with ethyl diazoacetate catalysed by ruthenium porphyrin complexes
Galardon, E
LeMaux, P
Simonneaux, G
[J]. CHEMICAL COMMUNICATIONS, 1997, (10) : 927 - 928
[10] First utilization of a homochiral ruthenium porphyrin as enantioselective epoxidation catalyst
Gross, Z
Ini, S
Kapon, M
Cohen, S
[J]. TETRAHEDRON LETTERS, 1996, 37 (40) : 7325 - 7328

← 1 2 3 →