Alkylation of lithium dienediolates of butenoic acids. Regioselectivity effects of structure and leaving group of the alkylating agent.

被引：35

作者：

Aurell, MJ ^{[1
]}

Gil, S ^{[1
]}

Mestres, R ^{[1
]}

Parra, M ^{[1
]}

Parra, L ^{[1
]}

机构：

[1] Univ Valencia, Dept Quim Organ, E-46100 Valencia, Spain

来源：

TETRAHEDRON | 1998年 / 54卷 / 17期

关键词：

D O I：

10.1016/S0040-4020(98)00149-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Regioselectivity of alkylation of but-2-enoic acids 1 and 2 by alkyl halides strongly depends on the reactivity of the electrophile. High a selectivity results for saturated alkyl halides, whereas poor a-selectivity is obtained for highly reactive allyl and benzyl halides. For reactive alkylating halides selectivity is partly governed by the ion pairing aggregates of the dienediolates. Lithium bromide and the carboxylate generated in the ongoing reaction cause opposite effects on regioselectivity. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：4357 / 4366

页数：10

共 29 条

[1] SILICON-DIRECTED SELECTIVE GAMMA SUBSTITUTION OF AN ALPHA,BETA-UNSATURATED ESTER
ALBAUGHROBERTSON, P
KATZENELLENBOGEN, JA
[J]. TETRAHEDRON LETTERS, 1982, 23 (07) : 723 - 726
[2] AURELL MJ, 1994, AN QUIM, V90, P457
[3] IODINE OXIDATIVE COUPLING OF DIENE AND TRIENE-DIOLATES OF UNSATURATED CARBOXYLIC-ACIDS
AURELL, MJ
GIL, S
PARRA, M
TORTAJADA, A
MESTRES, R
[J]. TETRAHEDRON, 1991, 47 (10-11) : 1997 - 2004
[4] Aurell MJ, 1997, TETRAHEDRON, V53, P10883
[5] DIENEDIOLATES OF UNSATURATED CARBOXYLIC-ACIDS IN SYNTHESIS - SYNTHESIS OF CYCLOHEXENONES AND POLYCYCLIC KETONES BY TANDEM MICHAEL-DIECKMANN DECARBOXYLATIVE ANNULATION OF UNSATURATED CARBOXYLIC-ACIDS
AURELL, MJ
GAVINA, P
MESTRES, R
[J]. TETRAHEDRON, 1994, 50 (08) : 2571 - 2582
[6] C-13 NMR-STUDIES OF DIANIONS OF UNSATURATED CARBOXYLIC-ACIDS
AURELL, MJ
GIL, S
MESTRES, R
PARRA, M
TORTAJADA, A
[J]. TETRAHEDRON, 1994, 50 (17) : 5109 - 5118
[7] CAREY FA, 1990, ADV ORG CHEM, VB, P23
[8] Studies on the reactivity of methyl gamma-tosylcrotonoate as ambident reagent in organic synthesis
Caturla, F
Najera, C
[J]. TETRAHEDRON, 1996, 52 (48) : 15243 - 15256
[9] CRAINE D, 1991, COMPREHENSIVE ORGANI, V3, P50
[10] Theoretical model of solvated lithium dienediolates of methyl substituted 2-butenoic acids
Domingo, LR
Gil, S
Mestres, R
Picher, MT
[J]. TETRAHEDRON, 1996, 52 (33) : 11105 - 11112

← 1 2 3 →