SUCCESSFUL APPLICATION OF ALPHA-HALOALLYLLITHIUM FOR A SIMPLE, CONVENIENT PREPARATION OF ALPHA-HALOALLYLBORONATE ESTER

被引：20

作者：

BROWN, HC ^{[1
]}

RANGAISHENVI, MV ^{[1
]}

机构：

[1] PURDUE UNIV,RICHARD B WETHERILL LAB CHEM,W LAFAYETTE,IN 47907

来源：

TETRAHEDRON LETTERS | 1990年 / 31卷 / 49期

关键词：

D O I：

10.1016/S0040-4039(00)97254-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first successful application of α-haloallyllithium, LiCH(X)CH=CH2, conveniently generated in situ from allyl halide and LDA in THF at -78 °C, for reaction with triisopmpyl borate to produce the valuable intermediate, α-haloallylboronate ester, is described. © 1990.

引用

页码：7113 / 7114

页数：2

共 14 条

[1] ORGANOBORANES .46. NEW PROCEDURES FOR THE HOMOLOGATION OF BORONIC ESTERS - A CRITICAL-EXAMINATION OF THE AVAILABLE PROCEDURES TO ACHIEVE CONVENIENT HOMOLOGATION OF BORONIC ESTERS [J].

BROWN, HC ;

SINGH, SM ;

RANGAISHENVI, MV .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (16) :3150-3155

[2]

Hase T. A., 1987, UMPOLED SYNTHONS

[3] TRANSFER OF CHIRALITY IN THE ADDITION OF CHIRAL ALPHA-CHLOROALLYLBORONATE ESTERS TO ALDEHYDES [J].

HOFFMANN, RW ;

LANDMANN, B .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1984, 23 (06) :437-438

[4] CHEMISTRY OF STABLE ALPHA-HALOGENOORGANOLITHIUM COMPOUNDS AND MECHANISM OF CARBENOID REACTIONS [J].

KOBRICH, G .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1967, 6 (01) :41-&

[5] ALPHA-HALOALLYLLITHIUM SPECIES - COUPLING WITH ALKYL BROMIDES [J].

MACDONALD, TL ;

NARAYANAN, BA ;

ODELL, DE .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (07) :1504-1506

[6] A PRACTICAL SYNTHESIS OF (DICHLOROMETHYL)BORONIC AND (1,1-DICHLOROETHYL)BORONIC ESTERS [J].

MATTESON, DS ;

HURST, GD .

ORGANOMETALLICS, 1986, 5 (07) :1465-1467

[7] DIRECTED CHIRAL SYNTHESIS BY WAY OF ALPHA-CHLORO BORONIC ESTERS [J].

MATTESON, DS ;

RAY, R ;

ROCKS, RR ;

TSAI, DJ .

ORGANOMETALLICS, 1983, 2 (11) :1536-1543

[8] LITHIUM 2,2,6,6-TETRAMETHYLPIPERIDIDE AND RELATED, STRONG, PROTON-SPECIFIC BASES - EVALUATION IN SYNTHESIS [J].

OLOFSON, RA ;

DOUGHERT.CM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (02) :582-584

[9] PREPARATION AND REACTIONS OF ESTERS OF DICHLOROMETHANEBORONIC ACID [J].

RATHKE, MW ;

CHAO, E ;

WU, G .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1976, 122 (02) :145-149

[10] (CHLOROMETHYL)LITHIUM - EFFICIENT GENERATION AND CAPTURE BY BORONIC ESTERS AND A SIMPLE PREPARATION OF DIISOPROPYL (CHLOROMETHYL)BORONATE [J].

SADHU, KM ;

MATTESON, DS .

ORGANOMETALLICS, 1985, 4 (09) :1687-1689

← 1 2 →