SYNTHESIS OF CHIRAL DIAZANEDICARBOXYLATE AND DIAZENEDICARBOXYLATE ESTERS - ELECTROPHILIC AMINATION REACTIONS OF ACHIRAL ESTER AND AMIDE ENOLATES

被引：24

作者：

HARRIS, JM ^{[1
]}

BOLESSA, EA ^{[1
]}

MENDONCA, AJ ^{[1
]}

FENG, SC ^{[1
]}

VEDERAS, JC ^{[1
]}

机构：

[1] UNIV ALBERTA,DEPT CHEM,EDMONTON,AB T6G 2G2,CANADA

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1995年 / 15期

关键词：

D O I：

10.1039/p19950001945

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of chiral dialkyl (bornyl, isobornyl, menthyl) diazenedicarboxylates 4a-c were prepared by conversion of the corresponding alcohols into chloroformates, condensation with hydrazine, and oxidation of the corresponding dialkyl diazanedicarboxylates 3a-c with N-bromosuccinimide and pyridine (50-90% yield). Their reaction with achiral enolates of esters and N,N-dimethyl amides at - 78 degrees C gave alpha-hydrazino acid derivatives with little or no stereoselectivity. Analogous aminations of chiral oxazolidinone (Evans enolate) anions were highly selective, but were controlled exclusively by enolate geometry.

引用

收藏

页码：1945 / 1950

页数：6

相关论文

共 31 条

[1] EXAMINATION OF SYNTHETIC ROUTES TO MONOSUBSTITUTED DIIMIDES .2. SYNTHESIS OF T-BUTYL ARYL- AND ACYLAZOFORMATES - ACID-INDUCED CLEAVAGE OF THIONOCARBO-T-BUTOXY GROUP [J].

CARPINO, LA ;

TERRY, PH ;

CROWLEY, PJ .

JOURNAL OF ORGANIC CHEMISTRY, 1961, 26 (11) :4336-&

[2] SOLVENT EFFECT IN PERICYCLIC-REACTIONS .9. THE ENE REACTION [J].

DESIMONI, G ;

FAITA, G ;

RIGHETTI, PP ;

SFULCINI, A ;

TSYGANOV, D .

TETRAHEDRON, 1994, 50 (06) :1821-1832

[3] EFFECT OF THE ACIDIC COMPONENT ON THE MITSUNOBU INVERSION OF A STERICALLY HINDERED ALCOHOL [J].

DODGE, JA ;

TRUJILLO, JI ;

PRESNELL, M .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (01) :234-236

[4] RECENT DEVELOPMENTS IN THE STEREOSELECTIVE SYNTHESIS OF ALPHA-AMINO-ACIDS [J].

DUTHALER, RO .

TETRAHEDRON, 1994, 50 (06) :1539-1650

[5] STEREOSELECTIVE AMINATION OF CHIRAL ENOLATES - A NEW APPROACH TO THE ASYMMETRIC-SYNTHESIS OF ALPHA-HYDRAZINO AND ALPHA-AMINO-ACID DERIVATIVES [J].

EVANS, DA ;

BRITTON, TC ;

DOROW, RL ;

DELLARIA, JF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (20) :6395-6397

[6] ENANTIOSELECTIVE ALDOL CONDENSATIONS .2. ERYTHRO-SELECTIVE CHIRAL ALOL CONDENSATIONS VIA BORON ENOLATES [J].

EVANS, DA ;

BARTROLI, J ;

SHIH, TL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (08) :2127-2129

[7] CONTRASTERIC CARBOXIMIDE HYDROLYSIS WITH LITHIUM HYDROPEROXIDE [J].

EVANS, DA ;

BRITTON, TC ;

ELLMAN, JA .

TETRAHEDRON LETTERS, 1987, 28 (49) :6141-6144

[8] THE ASYMMETRIC-SYNTHESIS OF ALPHA-AMINO AND ALPHA-HYDRAZINO ACID-DERIVATIVES VIA THE STEREOSELECTIVE AMINATION OF CHIRAL ENOLATES WITH AZODICARBOXYLATE ESTERS [J].

EVANS, DA ;

BRITTON, TC ;

DOROW, RL ;

DELLARIA, JF .

TETRAHEDRON, 1988, 44 (17) :5525-5540

[9]

EVANS DA, 1984, ASYMMETRIC SYNTHESIS, V3, P1

[10] CHEMISTRY OF ALPHA-CARBONYL AZO COMPOUNDS [J].

FAHR, E ;

LIND, H .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1966, 5 (04) :372-&

← 1 2 3 4 →