Telluro-directed regiospecific and highly stereoselective reaction of ethyl 5-telluro-(2E,4Z)-pentadienoate with organocopper reagents

被引：15

作者：

Huang, YZ ^{[1
]}

Mo, XS ^{[1
]}

Wang, L ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Organomet Chem Lab, Shanghai 200032, Peoples R China

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 5-6期

基金：

中国国家自然科学基金;

关键词：

D O I：

10.1016/S0040-4039(97)10571-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Ethyl 5-telluro-(2E,4Z)-pentadienoate 2, which is prepared by the Wittig olefination of (Z)-beta-telluroacrolein 1, reacted very rapidly with organocuprates 3 at -78 degrees C to form exclusively the corresponding 5-substituted products 4 with high stereoselectivity and in excellent yields. (C) 1997 Elsevier Science Ltd. All rights reserved.

引用

页码：419 / 422

页数：4

共 26 条

[1] VINYLLITHIUMS FROM BUTYL-VINYL TELLURIDES AND BIS-VINYL TELLURIDES [J].

BARROS, SM ;

COMASSETO, JV ;

BERRIEL, J .

TETRAHEDRON LETTERS, 1989, 30 (52) :7353-7356

[2]

CHIEFFI A, 1995, SYNLETT, P671

[3] INFLUENCE OF THE GEGENION IN THE TRANSMETALATION REACTION OF VINYLIC TELLURIDES WITH HIGHER-ORDER CYANOCUPRATES [J].

CHIEFFI, A ;

COMASSETO, JV .

TETRAHEDRON LETTERS, 1994, 35 (24) :4063-4066

[4]

COMASSETO JV, 1993, REV HETEROATOM CHEM, V9, P61

[5]

HIRO T, 1987, ANGEW CHEM INT EDIT, V26, P1187

[6]

HIRO T, 1987, ANGEW CHEM, V99, P1221

[7]

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

[8]

LANG RW, ORG SYNTHESIS COL, V7, P232

[9] THE CHEMISTRY OF HIGHER-ORDER ORGANOCUPRATES [J].

LIPSHUTZ, BH ;

WILHELM, RS ;

KOZLOWSKI, JA .

TETRAHEDRON, 1984, 40 (24) :5005-5038

[10] CONJUGATE ADDITION-REACTIONS OF ALPHA,BETA-UNSATURATED ESTERS WITH HIGHER-ORDER CUPRATES R2CU(CN)LI2 [J].

LIPSHUTZ, BH .

TETRAHEDRON LETTERS, 1983, 24 (02) :127-130

← 1 2 3 →