N-H insertion reactions of rhodium carbenoids .2. Preparation of N-substituted amino(phosphoryl)acetates (N-substituted phosphorylglycine esters)

被引:54
作者
Ferris, L
Haigh, D
Moody, CJ
机构
[1] LOUGHBOROUGH UNIV TECHNOL,DEPT CHEM,LOUGHBOROUGH LE11 3TU,LEICS,ENGLAND
[2] SMITHKLINE BEECHAM PHARMACEUT,EPSOM KT18 5XQ,SURREY,ENGLAND
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1996年 / 24期
关键词
D O I
10.1039/p19960002885
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Rhodium(II) acetate-catalysed reaction of ethyl 2-diazo-2-diethoxyphosphorylacetate 2 with carbamates, amides, ureas or anilines gives a range of N-substituted 2-amino-2-diethoxyphosphorylacetates 3-18 by N-H insertion reaction of the intermediate rhodium carbenoid.
引用
收藏
页码:2885 / 2888
页数:4
相关论文
共 51 条
[1]   STEREOSELECTIVE SYNTHESIS OF (E) AND (Z)-1-AZABICYCLO[3.1.0]HEX-2-YLIDENE DEHYDROAMINO ACID-DERIVATIVES [J].
ARMSTRONG, RW ;
TELLEW, JE ;
MORAN, EJ .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (08) :2208-2211
[2]   Mono-osmylation of dehydroamino acid dienes: Synthesis of dehydroamino acids related to the azinomycins [J].
Armstrong, RW ;
Tellew, JE ;
Moran, EJ .
TETRAHEDRON LETTERS, 1996, 37 (04) :447-450
[3]   SYNTHESIS OF L-ORNITHINES STEREOSPECIFICALLY DEUTERATED AT C-3 [J].
BALDWIN, JE ;
MERRITT, KD ;
SCHOFIELD, CJ .
TETRAHEDRON LETTERS, 1993, 34 (24) :3919-3920
[4]  
BARTELS G, 1980, LIEBIGS ANN CHEM, P168
[5]   SYNTHESIS OF ETHYL 3-METHYL-7-OXO-4-OXA-1-AZABICYCLO[3.2.0]HEPT-2-ENE-2-CARBOXYLATE AND THE REACTION OF 4-ACETOXYAZETIDIN-2-ONE WITH ETHYL ALPHA-DIAZOACETOACETATE [J].
BROOKS, G ;
HOWARTH, TT ;
HUNT, E .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1981, (13) :642-643
[6]  
CIATTINI PG, 1988, SYNTHESIS-STUTTGART, P140
[7]   STEREOSELECTIVE BROMINATION OF DEHYDROAMINO ACIDS WITH CONTROLLABLE RETENTION OR INVERSION OF OLEFIN CONFIGURATION [J].
COLEMAN, RS ;
CARPENTER, AJ .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (16) :4452-4461
[8]  
COLVIN EW, 1982, TETRAHEDRON LETT, V23, P3835, DOI 10.1016/S0040-4039(00)87720-5
[9]   RHODIUM-CARBENOID MEDIATED O-H INSERTION REACTIONS - O-H INSERTION VS H-ABSTRACTION AND EFFECT OF CATALYST [J].
COX, GG ;
MILLER, DJ ;
MOODY, CJ ;
SIE, ERHB ;
KULAGOWSKI, JJ .
TETRAHEDRON, 1994, 50 (10) :3195-3212
[10]  
DAUMAS M, 1990, SYNTHETIC COMMUN, V22, P3395