BETA-BORONATE CARBONYL DERIVATIVES - SYNTHESIS AND EVIDENCE FOR THE INTERVENTION OF BORONATE ATE-COMPLEXES IN ENOLATE ALKYLATIONS

被引：26

作者：

MEARS, RJ ^{[1
]}

WHITING, A ^{[1
]}

机构：

[1] UNIV MANCHESTER,INST SCI & TECHNOL,DEPT CHEM,MANCHESTER M60 1QD,LANCS,ENGLAND

来源：

TETRAHEDRON | 1993年 / 49卷 / 01期

关键词：

D O I：

10.1016/S0040-4020(01)80517-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Halomethylboronate derivatives form ''ate''-complexes with lithium ester enolates, which are relatively stable at room temperature and can be observed by B-11 n.m.r Reaction of an iodomethylboronate derivative with either an ester, ketone or amide enolate provides the corresponding beta-boronate carbonyl derivatives in 43-83% yield.

引用

页码：177 / 186

页数：10

共 13 条

[1] ORGANOBORANES .53. A HIGH-FIELD VARIABLE-TEMPERATURE H-1 AND B-11 NMR-STUDY OF THE EFFECTS OF SOLVENT AND STRUCTURE ON REACTIVITY IN ALLYLBORATION [J].

BROWN, HC ;

RACHERLA, US ;

PELLECHIA, PJ .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (06) :1868-1874

[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] STEREOSELECTIVE ALDOL REACTIONS OF BETA-BORONATE CARBONYL DERIVATIVES [J].

CURTIS, ADM ;

WHITING, A .

TETRAHEDRON LETTERS, 1991, 32 (11) :1507-1510

[4]

Evans D. A, 1984, ASYMMETRIC SYNTHES B, V3, P2

[5] SYNTHESIS OF 2-AMINO-3-BORONOPROPIONIC ACID - A BORON-CONTAINING ANALOG OF ASPARTIC-ACID [J].

KINDER, DH ;

AMES, MM .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (12) :2452-2454

[6] ALPHA-CHLORO BORONIC ESTERS FROM HOMOLOGATION OF BORONIC ESTERS [J].

MATTESON, DS ;

MAJUMDAR, D .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (25) :7588-7590

[7]

NOTH H, 1978, NMR SPECTROSCOPY BOR

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

RATHKE, MW ;

CHAO, E ;

WU, G .

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

[9] (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

[10] STRUCTURES OF 3 LITHIUM ESTER ENOLATES BY X-RAY-DIFFRACTION - DERIVATION OF REACTION-PATH FOR CLEAVAGE INTO KETENE AND ALCOHOLATE [J].

SEEBACH, D ;

AMSTUTZ, R ;

LAUBE, T ;

SCHWEIZER, WB ;

DUNITZ, JD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (19) :5403-5409

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