Highly enantioselective cyclopropanation of styrene derivatives using Co(III)-salen complex as a catalyst

被引：139

作者：

Fukuda, T ^{[1
]}

Katsuki, T ^{[1
]}

机构：

[1] KYUSHU UNIV 33,FAC SCI,DEPT CHEM,HIGASHI KU,FUKUOKA 81281,JAPAN

来源：

TETRAHEDRON | 1997年 / 53卷 / 21期

关键词：

D O I：

10.1016/S0040-4020(97)00423-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Optically active (salen)cobalt(III) bromide complex 6-Br was found to be an efficient catalyst for asymmetric cyclopropanation of styrene derivatives. For example, the reaction of 4-chlorostyrene and tert-butyl diazoacetate in the presence of 6-Br proceeded with high enantioselectivity of 96% ee as well as high trans-cis selectivity (97:3) to give tert-butyl 2-(4-chlorophenyl)cyclopropane-1-carboxylate as a major product. (C) 1997 Elsevier Science Ltd.

引用

页码：7201 / 7208

页数：8

共 43 条

[1] SYNTHESIS OF OPTICALLY-ACTIVE COBALT(SALEN) TYPE COMPLEXES AND THEIR ASYMMETRIC REACTIVITY TOWARD PROPYLENE-OXIDE
AOI, H
ISHIMORI, M
YOSHIKAWA, S
TSURUTA, T
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1975, 85 (02) : 241 - 248
[2] CATALYTIC ASYMMETRIC-SYNTHESIS OF CYCLOPROPANE-CARBOXYLIC ACIDS - AN APPLICATION OF CHIRAL COPPER CARBENOID REACTION
ARATANI, T
[J]. PURE AND APPLIED CHEMISTRY, 1985, 57 (12) : 1839 - 1844
[3] ARATANI T, 1975, TETRAHEDRON LETT, P1707
[4] ASYMMETRIC-SYNTHESIS OF PERMETHRIC ACID - STEREOCHEMISTRY OF CHIRAL COPPER CARBENOID REACTION
ARATANI, T
YONEYOSHI, Y
NAGASE, T
[J]. TETRAHEDRON LETTERS, 1982, 23 (06) : 685 - 688
[5] ARATANI T, 1977, TETRAHEDRON LETT, P2599
[6] THE OXYGEN-CARRYING SYNTHETIC CHELATE COMPOUNDS .7. PREPARATION
BAILES, RH
CALVIN, M
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1947, 69 (08) : 1886 - 1893
[7] SELECTIVE REACTIONS BETWEEN PHENOLS AND FORMALDEHYDE - A NOVEL ROUTE TO SALICYLALDEHYDES
CASIRAGHI, G
CASNATI, G
PUGLIA, G
SARTORI, G
TERENGHI, G
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1980, (09): : 1862 - 1865
[8] CHIRAL RHODIUM(II) CARBOXAMIDES - A NEW CLASS OF CATALYSTS FOR ENANTIOSELECTIVE CYCLOPROPANATION REACTIONS
DOYLE, MP
BRANDES, BD
KAZALA, AP
PIETERS, RJ
JARSTFER, MB
WATKINS, LM
EAGLE, CT
[J]. TETRAHEDRON LETTERS, 1990, 31 (46) : 6613 - 6616
[9] DIRHODIUM(II) TETRAKIS(CARBOXAMIDATES) WITH CHIRAL LIGANDS - STRUCTURE AND SELECTIVITY IN CATALYTIC METAL CARBENE TRANSFORMATIONS
DOYLE, MP
WINCHESTER, WR
HOORN, JAA
LYNCH, V
SIMONSEN, SH
GHOSH, R
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (22) : 9968 - 9978
[10] BIS(OXAZOLINES) AS CHIRAL LIGANDS IN METAL-CATALYZED ASYMMETRIC REACTIONS - CATALYTIC, ASYMMETRIC CYCLOPROPANATION OF OLEFINS
EVANS, DA
WOERPEL, KA
HINMAN, MM
FAUL, MM
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (02) : 726 - 728

← 1 2 3 4 5 →