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 [J].

COREY, EJ ;

IMWINKELRIED, R ;

PIKUL, S ;

XIANG, YB .

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 [J].

EVANS, DA ;

WOERPEL, KA ;

HINMAN, MM ;

FAUL, MM .

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 [J].

ITO, K ;

KATSUKI, T .

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 [J].

KOBAYASHI, S ;

TOKUNOH, R ;

SHIBASAKI, M ;

SHINAGAWA, R ;

MURAKAMIMUROFUSHI, K .

TETRAHEDRON LETTERS, 1993, 34 (25) :4047-4050

[6] ASYMMETRIC CATALYTIC CYCLOPROPANATION OF OLEFINS - BIS-OXAZOLINE COPPER-COMPLEXES [J].

LOWENTHAL, RE ;

ABIKO, A ;

MASAMUNE, S .

TETRAHEDRON LETTERS, 1990, 31 (42) :6005-6008

[7]

MURAKAMIMUROFUSHI K, 1992, J BIOL CHEM, V267, P21512

[8] OPTICALLY-ACTIVE CYCLOPROPANES [J].

SALAUN, J .

CHEMICAL REVIEWS, 1989, 89 (05) :1247-1270

[9] SYNTHESIS OF 4 DIASTEREOMERIC L-2-(CARBOXYCYCLOPROPYL)GLYCINES - CONFORMATIONALLY CONSTRAINED L-GLUTAMATE ANALOGS [J].

SHIMAMOTO, K ;

ISHIDA, M ;

SHINOZAKI, H ;

OHFUNE, Y .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (13) :4167-4176

[10]

TAKAHASHI H, 1992, TETRAHEDRON, V48, P5691

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