ENOLIZATION OF KETONES BY DIALKYLBORON CHLORIDES AND TRIFLATES - A MODEL FOR THE EFFECT OF REAGENT LEAVING GROUP, SUBSTRATE STRUCTURE AND AMINE BASE

被引：25

作者：

GOODMAN, JM

PATERSON, I

机构：

[1] University Chemical Laboratory, Cambridge, CB2 1EW, Lensfwid Road

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 47期

关键词：

D O I：

10.1016/S0040-4039(00)60878-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The contrasting regio- and stereoselectivities shown in-the kinetic enolisation of acyclic ketones by dialkylboron chlorides and triflates are rationalised by considering the conformations and electronic properties of the intermediate C=O.L2BX complexes.

引用

收藏

页码：7223 / 7226

页数：4

相关论文

共 18 条

[1] ENOLBORATION .2. DICYCLOHEXYLCHLOROBORANE TRIETHYLAMINE AS A CONVENIENT REAGENT FOR REGIOSELECTIVE AND STEREOSELECTIVE ENOLBORATION OF REPRESENTATIVE CLASSES OF KETONES [J].

BROWN, HC ;

DHAR, RK ;

GANESAN, K ;

SINGARAM, B .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (09) :2716-2721

[2] MAJOR EFFECT OF THE LEAVING GROUP IN DIALKYLBORON CHLORIDES AND TRIFLATES IN CONTROLLING THE STEREOSPECIFIC CONVERSION OF KETONES INTO EITHER (E)-ENOL OR (Z)-ENOL BORINATES [J].

BROWN, HC ;

DHAR, RK ;

BAKSHI, RK ;

PANDIARAJAN, PK ;

SINGARAM, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (09) :3441-3442

[3] ENOLBORATION .1. DICYCLOHEXYLCHLOROBORANE TRIETHYLAMINE AS A CONVENIENT REAGENT FOR ENOLBORATION OF KETONES AND OTHER CARBONYL DERIVATIVES [J].

BROWN, HC ;

DHAR, RK ;

GANESAN, K ;

SINGARAM, B .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (02) :499-504

[4] VERSATILE CHIRAL REAGENT FOR THE HIGHLY ENANTIOSELECTIVE SYNTHESIS OF EITHER ANTI OR SYN ESTER ALDOLS [J].

COREY, EJ ;

KIM, SS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (12) :4976-4977

[5] STEREOSELECTIVE ALDOL CONDENSATIONS VIA BORON ENOLATES [J].

EVANS, DA ;

NELSON, JV ;

VOGEL, E ;

TABER, TR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (11) :3099-3111

[6]

GENNARI C, 1992, J ORG CHEM, V57

[7] A FORCE-FIELD MODEL FOR BORON ENOLATES [J].

GOODMAN, JM ;

PATERSON, I ;

KAHN, SD .

TETRAHEDRON LETTERS, 1987, 28 (43) :5209-5212

[8] MOLECULAR-ORBITAL CALCULATIONS ON R1R2C = O.H2BF COMPLEXES - ANOMERIC STABILIZATION AND CONFORMATIONAL PREFERENCES [J].

GOODMAN, JM .

TETRAHEDRON LETTERS, 1992, 33 (47) :7219-7222

[9] THEORETICAL-STUDIES OF ALDOL STEREOSELECTIVITY - THE DEVELOPMENT OF A FORCE-FIELD MODEL FOR ENOL BORINATES AND THE INVESTIGATION OF CHIRAL ENOLATE PI-FACE SELECTIVITY [J].

GOODMAN, JM ;

KAHN, SD ;

PATERSON, I .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (10) :3295-3303

[10] REGIOSELECTIVE AND STEREOSELECTIVE CROSS-ALDOL REACTIONS VIA DIALKYLBORYL TRIFLATES [J].

INOUE, T ;

MUKAIYAMA, T .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1980, 53 (01) :174-178