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

被引：11

作者：

Aurell, MJ ^{[1
]}

Mestres, R ^{[1
]}

Muñoz, E ^{[1
]}

机构：

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

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 35期

关键词：

conjugate addition; carboxylic acids; organolithium;

D O I：

10.1016/S0040-4039(98)01306-9

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. Substitution by methyl groups at the alpha-carbon strongly decreases reactivity, whereas deprotonation of the starting acid occurs almost exclusively with methyl substitution at the beta-carbon of the 2-alkenoic acid. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：6351 / 6354

页数：4

共 22 条

[11]

Kozlowski J. A, 1991, COMPREHENSIVE ORGANI, V4, P169

[12]

KRUITHOF KJH, 1986, RECL TRAV CHIM PAY B, V105, P62

[13]

Lee V. J., 1991, COMPREHENSIVE ORGANI, V4, P69

[14]

MARCH J, 1992, ADV ORG CHEM, P797

[15]

MARCH J, 1992, ADV ORG CHEM, P931

[16]

O'Neil B. T., 1991, COMPREHENSIVE ORGANI, V1, P397

[17]

Perlmutter P., 1992, CONJUGATE ADDITION R

[18] Stereospecific 1,4-addition of organolithium reagents to unprotected 1- and 2-naphthalenecarboxylic acids. A facile route to 1,1,2- and -1,2,2-trisubstituted 1,2-dihydronaphthalenes [J].

Plunian, B ;

Mortier, J ;

Vaultier, M ;

Toupet, L .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (16) :5206-5207

[19]

Posner G. H., 1972, ORG REACTIONS, V19, P1

[20] 1,4-ADDITION REACTION OF ORGANOLITHIUM AND ORGANOMAGNESIUM COMPOUNDS TO ALPHA,BETA-UNSATURATED THIOAMIDES [J].

TAMARU, Y ;

HARADA, T ;

IWAMOTO, H ;

YOSHIDA, ZI .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (16) :5221-5223

← 1 2 3 →