OXIDATIVE ADDITION OF AZIDE ANION TO TRIISOPROPYLSILYL ENOL ETHERS - SYNTHESIS OF ALPHA-AZIDO KETONES

被引：32

作者：

MAGNUS, P

BARTH, L

机构：

[1] Department of Chemistry and Biochemistry, University of Texas at Austin, Austin

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 20期

基金：

美国国家卫生研究院;

关键词：

D O I：

10.1016/S0040-4039(00)78855-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Treatment of triisopropylsilyl enol ethers with ceric ammonium nitrate/sodium azide at -20-degrees-C in acetonitrile gives alpha-azido ketones in average to good yields (50-80%).

引用

页码：2777 / 2780

页数：4

共 23 条

[1] TOTAL, ASYMMETRIC-SYNTHESIS OF DEOXYPOLYOXIN-C [J].

AUBERSON, Y ;

VOGEL, P .

TETRAHEDRON, 1990, 46 (20) :7019-7032

[2]

EDWARDS OE, 1974, CAN J CHEM, V117, P1497

[3] ASYMMETRIC HALOGENATION OF CHIRAL IMIDE ENOLATES - A GENERAL-APPROACH TO THE SYNTHESIS OF ENANTIOMERICALLY PURE ALPHA-AMINO-ACIDS [J].

EVANS, DA ;

ELLMAN, JA ;

DOROW, RL .

TETRAHEDRON LETTERS, 1987, 28 (11) :1123-1126

[4] 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

[5] THE ASYMMETRIC-SYNTHESIS OF ALPHA-AMINO-ACIDS - ELECTROPHILIC AZIDATION OF CHIRAL IMIDE ENOLATES, A PRACTICAL APPROACH TO THE SYNTHESIS OF (R)-ALPHA-AZIDO AND (S)-ALPHA-AZIDO CARBOXYLIC-ACIDS [J].

EVANS, DA ;

BRITTON, TC ;

ELLMAN, JA ;

DOROW, RL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (10) :4011-4030

[6] 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

[7] ELECTROPHILIC AZIDE TRANSFER TO CHIRAL ENOLATES - A GENERAL-APPROACH TO THE ASYMMETRIC-SYNTHESIS OF ALPHA-AMINO-ACIDS [J].

EVANS, DA ;

BRITTON, TC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (22) :6881-6883

[8] ASYMMETRIC ELECTROPHILIC AMINATION - SYNTHESIS OF ALPHA-AMINO AND ALPHA-HYDRAZINO ACIDS WITH HIGH OPTICAL PURITY [J].

GENNARI, C ;

COLOMBO, L ;

BERTOLINI, G .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (20) :6394-6395

[9] ENANTIOSPECIFIC AND DIASTEREOSELECTIVE SYNTHESIS OF ANTI-ALPHA-HYDRAZINO-BETA-HYDROXYACIDS AND ALPHA-AMINO-BETA-HYDROXYACIDS THROUGH ELECTROPHILIC AMINATION OF BETA-HYDROXYESTERS [J].

GUANTI, G ;

BANFI, L ;

NARISANO, E .

TETRAHEDRON, 1988, 44 (17) :5553-5562

[10] STEREOSELECTIVE PREPARATION OF SYNTHETIC EQUIVALENTS OF 2-DEOXY-2-AMINO-AMINOTETROSES AND 3-DEOXY-3-AMINOTETROSES FROM MALIC-ACID - APPLICATION TO THE SYNTHESIS OF C18-D-RIBO-PHYTOSPHINGOSINE [J].

GUANTI, G ;

BANFI, L ;

NARISANO, E .

TETRAHEDRON LETTERS, 1989, 30 (40) :5507-5510

← 1 2 3 →