Nickel-catalyzed intermolecular coupling of 1,3-dienes and aldehydes via transmetalation of nickelacycles with diisobutylaluminum acetylacetonate

被引：55

作者：

Sato, Y ^{[1
]}

Sawaki, R ^{[1
]}

Saito, N ^{[1
]}

Mori, M ^{[1
]}

机构：

[1] Hokkaido Univ, Grad Sch Pharmaceut Sci, Sapporo, Hokkaido 0600812, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2002年 / 67卷 / 03期

关键词：

D O I：

10.1021/jo0106086

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Intermolecular coupling reactions of 1,3-dienes and aldehydes via transmetalation of nickelacycle intermediate with (BU2Al)-B-i-acac were investigated. In the reactions, a linear adduct or a branched adduct was produced, depending upon the nature of 1,3-dienes and aldehydes, via two nickelacycles that were relatively stable among the four possible nickelacycles because of the equilibrium with pi-allynickel forms.

引用

页码：656 / 662

页数：7

共 37 条

[1] REGIOSPECIFICITY IN REACTIONS OF BIS-PI-ALLYLNICKEL INTERMEDIATES WITH NUCLEOPHILIC AND ELECTROPHILIC REAGENTS [J].

BAKER, R ;

COOK, AH ;

CRIMMIN, MJ .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1975, (17) :727-728

[2] FORMATION OF ALCOHOLS FROM THE REACTIONS OF BUTA-1,3-DIENE AND ISOPRENE WITH ALDEHYDES CATALYZED BY NICKEL-COMPLEXES [J].

BAKER, R ;

CRIMMIN, MJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1979, (05) :1264-1267

[3] NICKEL EFFECT [J].

FISCHER, K ;

JONAS, K ;

MISBACH, P ;

STABBA, R ;

WILKE, G .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1973, 12 (12) :943-953

[4] CYCLOOLIGOMERIZATION WITH TRANSITION-METAL CATALYSTS [J].

HEIMBACH, P .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1973, 12 (12) :975-989

[5]

Heimbach P., 1970, ADVAN ORGANOMETAL CH, V8, P29

[6] NICKEL-MEDIATED ELIMINATION OF HYDROGEN HALIDE FROM PRIMARY AND SECONDARY ALKYL BROMIDES AND IODIDES - SYNTHETIC ASPECTS [J].

HENNINGSEN, MC ;

JEROPOULOS, S ;

SMITH, EH .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (13) :3015-3018

[7]

Jolly P.W., 1975, ORGANIC CHEM NICKEL, P1, DOI DOI 10.1016/B978-0-12-395719-1.50008-2

[8]

JOLLY PW, 1982, COMPREHENSIVE ORGANO, V8, P613

[9]

KEIM W, 1982, COMPREHENSIVE ORGANO, V8, P371

[10] Novel and highly regio- and stereoselective nickel-catalyzed homoallylation of benzaldehyde with 1,3-dienes [J].

Kimura, M ;

Ezoe, A ;

Shibata, K ;

Tamaru, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (16) :4033-4034

← 1 2 3 4 →