Formation of (Z) dialkylboron enolates from enolsilanes: Stereoconvergent transmetallation and diastereoselective aldol reactions

被引：20

作者：

Duffy, JL ^{[1
]}

Yoon, TP ^{[1
]}

Evans, DA ^{[1
]}

机构：

[1] HARVARD UNIV,DEPT CHEM,CAMBRIDGE,MA 02138

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 51期

基金：

美国国家卫生研究院; 美国国家科学基金会;

关键词：

D O I：

10.1016/0040-4039(95)02015-H

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Transmetallation of (E) and (Z) enolsilanes using halodialkylborane (R(2)BX) reagents provides predominantly the (Z) dialkylboron enolate under mild conditions. These enolates afford high levels of syn selectivity in subsequent aldol reactions.

引用

页码：9245 / 9248

页数：4

共 17 条

[1] ENOLBORATION .4. AN EXAMINATION OF THE EFFECT OF THE LEAVING GROUP-(X) ON THE STEREOSELECTIVE ENOLBORATION OF KETONES WITH VARIOUS R2BX/ET3N - NEW REAGENTS FOR THE SELECTIVE GENERATION OF EITHER Z-ENOL OR E-ENOL BORINATES FROM REPRESENTATIVE KETONES [J].

BROWN, HC ;

GANESAN, K ;

DHAR, RK .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (01) :147-153

[2] DOUBLE STEREODIFFERENTIATING ALDOL REACTIONS - THE DOCUMENTATION OF PARTIALLY MATCHED ALDOL BOND CONSTRUCTIONS IN THE ASSEMBLAGE OF POLYPROPIONATE SYSTEMS [J].

EVANS, DA ;

DART, MJ ;

DUFFY, JL ;

RIEGER, DL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (35) :9073-9074

[3] 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

[4] DIASTEREOSELECTIVE ANTIALDOL REACTIONS OF CHIRAL ETHYL KETONES - ENANTIOSELECTIVE PROCESSES FOR THE SYNTHESIS OF POLYPROPIONATE NATURAL-PRODUCTS [J].

EVANS, DA ;

NG, HP ;

CLARK, JS ;

RIEGER, DL .

TETRAHEDRON, 1992, 48 (11) :2127-2142

[5] STEREOSELECTIVE ALDOL REACTIONS OF CHLOROTITANIUM ENOLATES - AN EFFICIENT METHOD FOR THE ASSEMBLAGE OF POLYPROPIONATE-RELATED SYNTHONS [J].

EVANS, DA ;

RIEGER, DL ;

BILODEAU, MT ;

URPI, F .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (03) :1047-1049

[6] ENOLBORATION .5. AN EXAMINATION OF THE EFFECTS OF AMINE, SOLVENT, AND OTHER REACTION PARAMETERS ON THE STEREOSELECTIVE ENOLBORATION OF KETONES WITH VARIOUS CHX(2)BX REAGENTS - AN OPTIMIZED PROCEDURE TO ACHIEVE THE STEREOSELECTIVE SYNTHESIS OF E-ENOL BORINATES FROM REPRESENTATIVE KETONES USING CHX(2)BCL/ET(3)N [J].

GANESAN, K ;

BROWN, HC .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (25) :7162-7169

[7] ENOLBORATION .7. DICYCLOHEXYLIODOBORANE, A HIGHLY STEREOSELECTIVE REAGENT FOR THE ENOLBORATION OF TERTIARY AMIDES - EFFECTS OF SOLVENT AND ALDOLIZATION TEMPERATURE ON STEREOCHEMISTRY IN ACHIEVING THE STEREOELECTIVE SYNTHESIS OF EITHER SYN OR ANTI ALDOLS [J].

GANESAN, K ;

BROWN, HC .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (24) :7346-7352

[8] STEREOSELECTIVE ALDOL CONDENSATIONS VIA ALKENYLOXYDIALKOXYBORANES - MECHANISTIC AND STEREOCHEMICAL DETAILS [J].

GENNARI, C ;

COLOMBO, L ;

SCOLASTICO, C ;

TODESCHINI, R .

TETRAHEDRON, 1984, 40 (20) :4051-4058

[9] EFFECTS OF LITHIUM-SALTS ON THE STEREOCHEMISTRY OF KETONE ENOLIZATION BY LITHIUM 2,2,6,6-TETRAMETHYLPIPERIDIDE (LITMP) - A CONVENIENT METHOD FOR HIGHLY E-SELECTIVE ENOLATE FORMATION [J].

HALL, PL ;

GILCHRIST, JH ;

COLLUM, DB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (25) :9571-9574

[10] ACYCLIC STEREOSELECTION .36. SIMPLE DIASTEREOSELECTION IN THE LEWIS ACID MEDIATED REACTIONS OF ENOL SILANES WITH ALDEHYDES [J].

HEATHCOCK, CH ;

DAVIDSEN, SK ;

HUG, KT ;

FLIPPIN, LA .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (15) :3027-3037

← 1 2 →