Conjugate addition of organolithium reagents to α,β-unsaturated carboxylic acids.

被引：19

作者：

Aurell, MJ ^{[1
]}

Domingo, LR ^{[1
]}

Mestres, R ^{[1
]}

Muñoz, E ^{[1
]}

Zaragozá, RJ ^{[1
]}

机构：

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

来源：

TETRAHEDRON | 1999年 / 55卷 / 03期

关键词：

conjugate addition; carboxylic acids; organolithium; PM3; calculations;

D O I：

10.1016/S0040-4020(98)01073-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Conjugate addition of primary, secondary, tertiary alkyl and phenyl lithium reagents to 2-alkenoic acids affords good yields of branched saturated carboxylic acids. Methyl groups at the alpha- and beta-carbon of the 2-alkenoic acid decrease reactivity as accepters, and foster deprotonation, respectively. The lithium enediolate resulting from the conjugate addition can react with electrophiles. PM3 calculations are in agreement with the substituent effects. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：815 / 830

页数：16

相关论文

共 44 条

[1] Direct easy synthesis of ketones from carboxylic acids and chlorinated compounds [J].

Alonso, F ;

Lorenzo, E ;

Yus, M .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (17) :6058-6059

[2] OPTIMIZATION AND APPLICATION OF LITHIUM PARAMETERS FOR PM3 [J].

ANDERS, E ;

KOCH, R ;

FREUNSCHT, P .

JOURNAL OF COMPUTATIONAL CHEMISTRY, 1993, 14 (11) :1301-1312

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

Aurell, MJ ;

Gil, S ;

Mestres, R ;

Parra, M ;

Parra, L .

TETRAHEDRON, 1998, 54 (17) :4357-4366

[4] Conjugate addition of organolithium reagents to α,β-unsaturated carboxylic acids. [J].

Aurell, MJ ;

Mestres, R ;

Muñoz, E .

TETRAHEDRON LETTERS, 1998, 39 (35) :6351-6354

[5] DIENEDIOLATES OF UNSATURATED CARBOXYLIC-ACIDS IN SYNTHESIS - SYNTHESIS OF CYCLOHEXENONES AND POLYCYCLIC KETONES BY TANDEM MICHAEL-DIECKMANN DECARBOXYLATIVE ANNULATION OF UNSATURATED CARBOXYLIC-ACIDS [J].

AURELL, MJ ;

GAVINA, P ;

MESTRES, R .

TETRAHEDRON, 1994, 50 (08) :2571-2582

[6]

AURELL MJ, 1995, SYNLETT, P459

[7] AN ALGORITHM FOR THE LOCATION OF TRANSITION-STATES [J].

BAKER, J .

JOURNAL OF COMPUTATIONAL CHEMISTRY, 1986, 7 (04) :385-395

[8] CONJUGATE ADDITION OF ORGANO-LITHIUM REAGENTS TO ACRYLANILIDE ANIONS [J].

BALDWIN, JE ;

DUPONT, WA .

TETRAHEDRON LETTERS, 1980, 21 (19) :1881-1882

[9] ORGANOBORANES FOR SYNTHESIS .14. CONVENIENT PROCEDURES FOR THE DIRECT OXIDATION OF ORGANOBORANES FROM TERMINAL ALKENES TO CARBOXYLIC-ACIDS [J].

BROWN, HC ;

KULKARNI, SV ;

KHANNA, VV ;

PATIL, VD ;

RACHERLA, US .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (23) :6173-6177

[10] CONJUGATE ADDITION-REACTIONS OF ALPHA-SILYLATED ALPHA,BETA-UNSATURATED CARBOXYLIC-ACID SALTS [J].

COOKE, MP .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (26) :5729-5733

← 1 2 3 4 5 →