EFFICIENT SYNTHESIS OF METHYL 2-(TERT-BUTYL)ACRYLATE AND ANALOGOUS ESTERS

被引：19

作者：

XU, LH ^{[1
]}

KUNDIG, EP ^{[1
]}

机构：

[1] UNIV GENEVA,DEPT CHIM ORGAN,CH-1211 GENEVA 4,SWITZERLAND

来源：

HELVETICA CHIMICA ACTA | 1994年 / 77卷 / 06期

关键词：

D O I：

10.1002/hlca.19940770603

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The title products are prepared via an efficient three-step synthesis which involves hydroalumination of methyl propiolate and Lewis-acid-promoted reaction with acetone in the presence of BF3 followed by two highly selective S(N)2' reactions. The key step is the reaction of 2-(chloromethyl)acrylates with R(2)CuLi/ZnCl2 reagents which takes place with complete allylic rearrangement.

引用

页码：1480 / 1484

页数：5

共 22 条

[21] HIGHER-ORDER ZINC CUPRATE REAGENTS - VERY HIGH 1,3-CHIRALITY TRANSFER-REACTION OF GAMMA-(MESYLOXY)-ALPHA,BETA-UNSATURATED CARBONYL DERIVATIVES [J].

YAMAMOTO, Y ;

CHOUNAN, Y ;

TANAKA, M ;

IBUKA, T .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (03) :1024-1026

[22] THE DIRECT FORMATION OF FUNCTIONALIZED ALKYL(ARYL)ZINC HALIDES BY OXIDATIVE ADDITION OF HIGHLY REACTIVE ZINC WITH ORGANIC HALIDES AND THEIR REACTIONS WITH ACID-CHLORIDES, ALPHA,BETA-UNSATURATED KETONES, AND ALLYLIC, ARYL, AND VINYL HALIDES [J].

ZHU, L ;

WEHMEYER, RM ;

RIEKE, RD .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (04) :1445-1453

← 1 2 3 →