The chemo- and enantioselective cyclopropanation of polyenes: Chiral auxiliary vs chiral reagent-based approach.

被引：34

作者：

Charette, AB

Juteau, H

Lebel, H

Deschenes, D

机构：

[1] Département de Chimie, Université de Montréal, Montréal

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 44期

基金：

加拿大自然科学与工程研究理事会;

关键词：

D O I：

10.1016/0040-4039(96)01798-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The chemo- and enantioselective cyclopropanation of allylic alcohols containing additional olefins was investigated using the dioxaborolane-derived reagent. High chemo- and enantioselectivities were usually observed if a mixture of the chiral dioxaborolane ligand/allylic alcohol was treated with a solution of Zn(CH2I)(2) . DME complex. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：7925 / 7928

页数：4

共 15 条

[1] BARRETT AGM, 1996, J CHEM SOC CHEM COMM, P325
[2] 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
[3] 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
[4] Stereoselective synthesis of all four isomers of coronamic acid: A general approach to 3-methanoamino acids
Charette, AB
Cote, B
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (51) : 12721 - 12732
[5] CHARETTE AB, UNPUB J AM CHEM SOC
[6] FRAENKEL G, 1979, J ORG CHEM, V44, P2522
[7] FURUKAWA J, 1970, TETRAHEDRON, V26, P243
[8] SYNTHESIS OF CYCLOPROPANES BY REACTION OF OLEFINS WITH DIALKYLZINC AND METHYLENE IODIDE
FURUKAWA, J
KAWABATA, N
NISHIMUR.J
[J]. TETRAHEDRON, 1968, 24 (01) : 53 - &
[9] Site and stereoselectivity of the cyclopropanation of unsymmetrically substituted 1,3-dienes by the Simmons-Smith reaction.
Guerreiro, MC
Schuchardt, U
[J]. SYNTHETIC COMMUNICATIONS, 1996, 26 (09) : 1793 - 1800
[10] DISCOVERY, ISOLATION, STRUCTURE ELUCIDATION, AND BIOSYNTHESIS OF U-106305, A CHOLESTERYL ESTER TRANSFER PROTEIN INHIBITOR FROM UC-11136
KUO, MS
ZIELINSKI, RJ
CIALDELLA, JI
MARSCHKE, CK
DUPUIS, MJ
LI, GP
KLOOSTERMAN, DA
SPILMAN, CH
MARSHALL, VP
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (43) : 10629 - 10634

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