Magnesium promoted cyclopropanation reactions of allylic alcohols

被引：30

作者：

Bolm, C ^{[1
]}

Pupowicz, D ^{[1
]}

机构：

[1] UNIV MARBURG,FACHBEREICH CHEM,D-35032 MARBURG,GERMANY

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 42期

关键词：

allylic alcohols; carbenoids; cyclopropanation; Grignard Reagents; magnesium;

D O I：

10.1016/S0040-4039(97)10009-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Treatment of allylic alcohols 1 with various magnesium reagents in the presence of alkyl dihalides affords the corresponding cyclopropyl alcohols 2. Reactions occur under mild conditions, and excellent diastereoselectivities have been achieved. (C) 1997 Elsevier Science Ltd.

引用

页码：7349 / 7352

页数：4

共 46 条

[1] SYNTHETIC STUDIES ON THE KEY COMPONENT OF THE NEW-GENERATION OF QUINOLONECARBOXYLIC ACID, DU-6859 .2. ASYMMETRIC-SYNTHESIS OF (1R,2S)-2-FLUOROCYCLOPROPYLAMINE
AKIBA, T
TAMURA, O
HASHIMOTO, M
KOBAYASHI, Y
KATOH, T
NAKATANI, K
KAMADA, M
HAYAKAWA, I
TERASHIMA, S
[J]. TETRAHEDRON, 1994, 50 (13) : 3905 - 3914
[2] AN ASYMMETRIC SIMMONS-SMITH REACTION
ARAI, I
MORI, A
YAMAMOTO, H
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (26) : 8254 - 8256
[3] BARRETT AGM, 1996, J CHEM SOC CHEM COMM, P325
[4] CYCLOPROPANE SYNTHESIS FROM METHYLENE IODIDE ZINC-COPPER COUPLE + OLEFINS .2. NATURE OF INTERMEDIATE
BLANCHARD, EP
SIMMONS, HE
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (07) : 1337 - &
[5] BURGESS K, 1994, SYNLETT, P575
[6] IMPROVED PROCEDURE FOR THE SYNTHESIS OF ENANTIOMERICALLY ENRICHED CYCLOPROPYLMETHANOL DERIVATIVES
CHARETTE, AB
PRESCOTT, S
BROCHU, C
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (04) : 1081 - 1083
[7] DESIGN OF AMPHOTERIC BIFUNCTIONAL LIGANDS - APPLICATION TO THE ENANTIOSELECTIVE SIMMONS-SMITH CYCLOPROPANATION OF ALLYLIC ALCOHOLS
CHARETTE, AB
JUTEAU, H
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (06) : 2651 - 2652
[8] A NEW STRATEGY FOR THE LEWIS ACID-CATALYZED CYCLOPROPANATION OF ALLYLIC ALCOHOLS
CHARETTE, AB
BROCHU, C
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (45) : 11367 - 11368
[9] DIASTEREOSELECTIVE CYCLOPROPANATION OF CHIRAL ALLYLIC ALCOHOLS - A MORE EFFICIENT REAGENT FOR THE RELATIVE STEREOCONTROL
CHARETTE, AB
LEBEL, H
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (10) : 2966 - 2967
[10] Diastereo- and enantioselective synthesis of 1,2,3-substituted cyclopropanes with zinc carbenoids
Charette, AB
Lemay, J
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (10): : 1090 - 1092

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