Effect of InCl3 on the addition of Grignard reagents to α,β-unsaturated carbonyl compounds

被引：16

作者：

Kelly, BG

Gilheany, DG ^{[1
]}

机构：

[1] Natl Univ Ireland Univ Coll Dublin, Dept Chem, Dublin 4, Ireland

[2] Natl Univ Ireland Univ Coll Dublin, Conway Inst Biomol & Biomed Sci, Dublin 4, Ireland

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 05期

关键词：

D O I：

10.1016/S0040-4039(01)02263-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Control of 1,2-versus 1,4-addition of organometallic reagents to enones remains a long-standing problem. There is still no satisfactory 1,2-directing agent comparable to the 1,4-directing effect of copper salts. We report that the presence of just 5 mol% indium(Ill) chloride can significantly alter the amount of 1,2-product formed in these reactions. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：887 / 890

页数：4

相关论文

共 19 条

[1] STUDIES ON THE MECHANISM OF CONJUGATE ADDITION .1. THE ADDITION OF GRIGNARD REAGENTS TO 2-CYCLOHEXENONE AND SOME OPEN CHAIN ANALOGS [J].

ALEXANDER, ER ;

CORAOR, GR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1951, 73 (06) :2721-2723

[2]

[Anonymous], 1985, ADV ORG CHEM

[3] SELECTIVE ALKYLATION AND ALLYLATION OF ALLYLIC HALIDES BY TETRAORGANOINDATES - REGIOSELECTIVE AND STEREOSELECTIVE SYNTHESIS OF ROSEFURAN AND SESQUIROSEFURAN [J].

ARAKI, S ;

JIN, SJ ;

BUTSUGAN, Y .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (05) :549-552

[4]

Babu G, 2000, ALDRICHIM ACTA, V33, P16

[5] Advances in indium-catalysed organic synthesis [J].

Chauhan, KK ;

Frost, CG .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (18) :3015-3019

[6]

CINTAS P, 1995, SYNLETT, P1087

[7] MECHANISM OF THE GRIGNARD ADDITION-REACTION .16. HOMOLYTIC AND CONCERTED MECHANISMS IN THE REACTION OF ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS WITH GRIGNARD-REAGENTS [J].

HOLM, T .

ACTA CHEMICA SCANDINAVICA, 1991, 45 (09) :925-929

[8] CHEMISTRY OF CARBANIONS .12. ROLE OF COPPER INCONJUGATE ADDITION OF ORGANOMETALLIC REAGENTS [J].

HOUSE, HO ;

RESPESS, WL ;

WHITESID.GM .

JOURNAL OF ORGANIC CHEMISTRY, 1966, 31 (10) :3128-&

[9] CHEMISTRY OF CARBANIONS .4. STEREOCHEMISTRY OF CONJUGATE GRIGNARD ADDITION [J].

HOUSE, HO ;

THOMPSON, HW .

JOURNAL OF ORGANIC CHEMISTRY, 1963, 28 (02) :360-&

[10] Aqueous Barbier-Grignard type reaction: Scope, mechanism, and synthetic applications [J].

Li, CJ .

TETRAHEDRON, 1996, 52 (16) :5643-5668