Chemoselective acylation of some oxidofunctionalised organolithium compounds

被引：6

作者：

Yus, M ^{[1
]}

Gomis, J ^{[1
]}

机构：

[1] Univ Alicante, Fac Ciencias, Dept Quim Organ, E-03080 Alicante, Spain

来源：

TETRAHEDRON | 2003年 / 59卷 / 27期

关键词：

lithiation; lithium and compounds; zinc and compounds; acylation; catalysis;

D O I：

10.1016/S0040-4020(03)00758-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Once oxidofunctionalised organolithium compounds 1 (easily prepared by reductive ring opening of isochroman and phthalan by DTBB-catalysed lithiation) were transmetallated with ZnBr2/CuCN.2LiCl and reacted successively with a carboxylic acid anhydride and an acyl chloride in THF at 0degreesC, the corresponding differently acylated compounds 4 were obtained after hydrolysis with water. The anhydride performed the O-acylation exclusively and the acyl chloride carried out the C-acylation. (C) 2003 Elsevier Science Ltd. All rights reserved.

引用

页码：4967 / 4971

页数：5

共 31 条

[1] LITHIUM 2-(2-LITHIOMETHYLPHENYL)ETHANOLATE FROM ISOCHROMAN - EASY PREPARATION OF SUBSTITUTED BENZOXEPINES AND FUNCTIONALIZED ARENES [J].

ALMENA, J ;

FOUBELO, F ;

YUS, M .

TETRAHEDRON, 1995, 51 (11) :3365-3374

[2] 1,2-DI(LITHIOMETHYL)BENZENE FROM PHTHALAN - SEQUENTIAL INTRODUCTION OF 2 DIFFERENT ELECTROPHILES [J].

ALMENA, J ;

FOUBELO, F ;

YUS, M .

TETRAHEDRON, 1995, 51 (11) :3351-3364

[3]

Boudier A, 2000, ANGEW CHEM INT EDIT, V39, P4414, DOI 10.1002/1521-3773(20001215)39:24<4414::AID-ANIE4414>3.0.CO

[4]

2-C

[5] GAS-PHASE UNIMOLECULAR ELIMINATION OF SOME ORTHO-SUBSTITUTED BETA-PHENYLETHYL ACETATES [J].

CHUCHANI, G ;

ROTINOV, A ;

CARABALLO, DF ;

MEDINA, JD .

REACTION KINETICS AND CATALYSIS LETTERS, 1980, 13 (02) :173-179

[6]

Clayden J., 2002, ORGANOLITHIUMS SELEC

[7]

ERDIK E, 1996, ORGANOZINC REAGENT O

[8] Highly efficient, general procedure for the preparation of alkylzinc reagents from unactivated alkyl bromides and chlorides [J].

Huo, SQ .

ORGANIC LETTERS, 2003, 5 (04) :423-425

[9] PREPARATION AND REACTIONS OF POLYFUNCTIONAL ORGANOZINC REAGENTS IN ORGANIC-SYNTHESIS [J].

KNOCHEL, P ;

SINGER, RD .

CHEMICAL REVIEWS, 1993, 93 (06) :2117-2188

[10]

Knochel P., 1999, ORGANOZINC REAGENTS

← 1 2 3 4 →