ENANTIOSELECTIVE CYCLOPROPANATION OF ALLYLIC ALCOHOLS CATALYZED BY A CHIRAL DISULFONAMIDE-ALUMINUM COMPLEX

被引：55

作者：

IMAI, N ^{[1
]}

TAKAHASHI, H ^{[1
]}

KOBAYASHI, S ^{[1
]}

机构：

[1] SAGAMI CHEM RES CTR, 4-4-1 NISHI OHNUMA, SAGAMIHARA, KANAGAWA 229, JAPAN

来源：

CHEMISTRY LETTERS | 1994年 / 01期

关键词：

D O I：

10.1246/cl.1994.177

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A chiral disulfonamide-alkylaluminum complex prepared from (1R,2R)-N,N'-bis(benzenesulfonyl)-1,2-cyclohexanediamine and trialkylaluminum or i-Bu2AlH has been found to catalyze a Simmons-Smith cyclopropanation of allylic alcohols with Et2Zn and CH2I2 to afford the corresponding cyclopropanes in excellent yields with high enantiomeric excesses.

引用

页码：177 / 180

页数：4

共 18 条

[1] PRACTICAL ENANTIOSELECTIVE DIELS-ALDER AND ALDOL REACTIONS USING A NEW CHIRAL CONTROLLER SYSTEM
COREY, EJ
IMWINKELRIED, R
PIKUL, S
XIANG, YB
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (14) : 5493 - 5495
[2] DENMARK SE, 1992, SYNTHESIS-STUTTGART, P229
[3] 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
[4] CATALYTIC ASYMMETRIC CYCLOPROPANATION USING COPPER COMPLEX OF OPTICALLY-ACTIVE BIPYRIDINE AS A CATALYST
ITO, K
KATSUKI, T
[J]. TETRAHEDRON LETTERS, 1993, 34 (16) : 2661 - 2664
[5] SYNTHESIS OF 1-O-ACYLGLYCEROL 2,3-CYCLIC PHOSPHATE - DETERMINATION OF THE ABSOLUTE STRUCTURE OF PHYLPA, A SPECIFIC INHIBITOR OF DNA-POLYMERASE ALPHA
KOBAYASHI, S
TOKUNOH, R
SHIBASAKI, M
SHINAGAWA, R
MURAKAMIMUROFUSHI, K
[J]. TETRAHEDRON LETTERS, 1993, 34 (25) : 4047 - 4050
[6] ASYMMETRIC CATALYTIC CYCLOPROPANATION OF OLEFINS - BIS-OXAZOLINE COPPER-COMPLEXES
LOWENTHAL, RE
ABIKO, A
MASAMUNE, S
[J]. TETRAHEDRON LETTERS, 1990, 31 (42) : 6005 - 6008
[7] MURAKAMIMUROFUSHI K, 1992, J BIOL CHEM, V267, P21512
[8] OPTICALLY-ACTIVE CYCLOPROPANES
SALAUN, J
[J]. CHEMICAL REVIEWS, 1989, 89 (05) : 1247 - 1270
[9] SYNTHESIS OF 4 DIASTEREOMERIC L-2-(CARBOXYCYCLOPROPYL)GLYCINES - CONFORMATIONALLY CONSTRAINED L-GLUTAMATE ANALOGS
SHIMAMOTO, K
ISHIDA, M
SHINOZAKI, H
OHFUNE, Y
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (13) : 4167 - 4176
[10] TAKAHASHI H, 1992, TETRAHEDRON, V48, P5691

← 1 2 →