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

页码：815 / 830

页数：16

共 44 条

[21]

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

[22]

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

[23]

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

[24]

MARCH J, 1992, ADV ORG CHEM, P797

[25]

MARCH J, 1992, ADV ORG CHEM, P931

[26]

MEYERS AI, 1975, J AM CHEM SOC, V97, P6266, DOI 10.1021/ja00854a065

[27] HIGHLY STEREOSELECTIVE ADDITION OF ORGANOLITHIUM REAGENTS TO CHIRAL OXAZOLINES - ASYMMETRIC SYNTHESIS OF 3-SUBSTITUTED ALKANOIC ACIDS AND 3-SUBSTITUTED LACTONES [J].

MEYERS, AI ;

SMITH, RK ;

WHITTEN, CE .

JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (13) :2250-2256

[28]

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

[29]

Perlmutter P., 1992, CONJUGATE ADDITION R

[30] 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

← 1 2 3 4 5 →