HOMOLOGATION OF REPRESENTATIVE BORONIC ESTERS USING IN-SITU GENERATED (HALOMETHYL)LITHIUMS - A COMPARATIVE-STUDY

被引：34

作者：

SOUNDARARAJAN, R ^{[1
]}

LI, GS ^{[1
]}

BROWN, HC ^{[1
]}

机构：

[1] PURDUE UNIV,HC BROWN & RB WETHERILL LABS CHEM,W LAFAYETTE,IN 47907

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 48期

基金：

美国国家科学基金会;

关键词：

D O I：

10.1016/0040-4039(94)88399-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A comparative study of the homologation of representative boronic esters with in situ generated LiCH(2)X (X = Cl; Br; I) is presented wherein the reactivity differences arising out of the steric and electronic effects of the migrating groups, and the nature of the ester groups are determined and discussed.

引用

页码：8957 / 8960

页数：4

共 11 条

[1] RING ENLARGEMENT OF BORACYCLANES VIA SEQUENTIAL ONE-CARBON HOMOLOGATION - THE 1ST SYNTHESIS OF BORACYCLANES IN THE STRAINED MEDIUM RING RANGE [J].

BROWN, HC ;

PHADKE, AS ;

RANGAISHENVI, MV .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (18) :6263-6264

[2] 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

[3] HIGHLY GENERAL-SYNTHESIS OF [E]- AND [Z]-3-ALKYLSUBSTITUTED ALLYLBORONATES VIA ONE-CARBON HOMOLOGATION OF STEREOSPECIFIC 1-ALKEN-1-YLBORONATES [J].

BROWN, HC ;

PHADKE, AS ;

BHAT, NG .

TETRAHEDRON LETTERS, 1993, 34 (49) :7845-7848

[4]

BROWN HC, 1991, SYNLETT, P631

[5] RECENT ADVANCES IN ASYMMETRIC-SYNTHESIS WITH BORONIC ESTERS [J].

MATTESON, DS .

PURE AND APPLIED CHEMISTRY, 1991, 63 (03) :339-344

[6] BORONIC ESTERS IN STEREODIRECTED SYNTHESIS [J].

MATTESON, DS .

TETRAHEDRON, 1989, 45 (07) :1859-1885

[7] SYNTHESIS OF L-(+)-RIBOSE VIA (S)-PINANEDIOL (ALPHA-S)-ALPHA-BROMO BORONIC ESTERS [J].

MATTESON, DS ;

PETERSON, ML .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (23) :5116-5121

[8]

MICHNICK TJ, 1991, SYNLETT, P631

[9] (CHLOROMETHYL) LITHIUM IN AN EFFICIENT CONVERSION OF CARBONYL-COMPOUNDS TO CHLOROHYDRINS OR OXIRANES [J].

SADHU, KM ;

MATTESON, DS .

TETRAHEDRON LETTERS, 1986, 27 (07) :795-798

[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

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