A CATALYTIC ENANTIOSELECTIVE REACTION USING A C2-SYMMETRICAL DISULFONAMIDE AS A CHIRAL LIGAND - CYCLOPROPANATION OF ALLYLIC ALCOHOLS BY THE ET2ZN-CH2I2-DISULFONAMIDE SYSTEM

被引：95

作者：

TAKAHASHI, H ^{[1
]}

YOSHIOKA, M ^{[1
]}

OHNO, M ^{[1
]}

KOBAYASHI, S ^{[1
]}

机构：

[1] UNIV TOKYO,FAC PHARMACEUT SCI,BUNKYO KU,TOKYO 113,JAPAN

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 18期

关键词：

CYCLOPROPANATION; SIMMONS-SMITH REACTION; CHIRAL LEWIS ACID; ENANTIOSELECTIVE REACTION; DISULFONAMIDE;

D O I：

10.1016/S0040-4039(00)92246-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first catalytic, enantioselective Simmons-Smith cyclopropanation of an allylic alcohol has been achieved by the reaction of an allylic alcohol with Et2Zn and CH2I2 in the presence of a catalytic amount of chiral disulfonamide 1.

引用

页码：2575 / 2578

页数：4

共 21 条

[1] AN ASYMMETRIC SIMMONS-SMITH REACTION
ARAI, I
MORI, A
YAMAMOTO, H
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (26) : 8254 - 8256
[2] ABSOLUTE CONFIGURATION OF CIS-2-PHENYLCYCLOPROPANE-CARBOXYLIC ACID AND RELATED COMPOUNDS
ARATANI, T
NAKANISI, Y
NOZAKI, H
[J]. TETRAHEDRON, 1970, 26 (07) : 1675 - &
[3] RELATIVE RATES AND STEREOCHEMISTRY OF IODOZINCMETHYL IODIDE METHYLENATION OF SOME HYDROXY- AND METHOXY-SUBSTITUTED CYCLIC OLEFINS
CHAN, JHH
RICKBORN, B
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (23) : 6406 - &
[4] 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
[5] SOLUTION AND SOLID-STATE STRUCTURE OF THE WITTIG-FURUKAWA CYCLOPROPANATION REAGENT
DENMARK, SE
EDWARDS, JP
WILSON, SR
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (02) : 723 - 725
[6] A COMPARISON OF (CHLOROMETHYL)ZINC AND (IODOMETHYL)ZINC CYCLOPROPANATION REAGENTS
DENMARK, SE
EDWARDS, JP
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (25) : 6974 - 6981
[7] 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
[8] TITANIUM(IV) CHLORIDE CATALYZED CYCLOPROPANATIONS OF ALKENES USING ZINC DUST, COPPER(I) CHLORIDE, AND DIHALOMETHANES
FRIEDRICH, EC
LUNETTA, SE
LEWIS, EJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (10) : 2388 - 2390
[9] SYNTHESIS OF CYCLOPROPANES BY REACTION OF OLEFINS WITH DIALKYLZINC AND METHYLENE IODIDE
FURUKAWA, J
KAWABATA, N
NISHIMUR.J
[J]. TETRAHEDRON, 1968, 24 (01) : 53 - &
[10] ENZYMATIC-HYDROLYSIS OF CYCLOPROPANES - TOTAL SYNTHESIS OF OPTICALLY PURE DICTYOPTERENE-A AND DICTYOPTERENE-C'
GRANDJEAN, D
PALE, P
CHUCHE, J
[J]. TETRAHEDRON, 1991, 47 (07) : 1215 - 1230

← 1 2 3 →