N-H insertion reactions of rhodium carbenoids .1. Preparation of alpha-amino acid and alpha-aminophosphonic acid derivatives

被引:77
作者
Aller, E
Buck, RT
Drysdale, MJ
Ferris, L
Haigh, D
Moody, CJ
Pearson, ND
Sanghera, JB
机构
[1] LOUGHBOROUGH UNIV TECHNOL,DEPT CHEM,LOUGHBOROUGH LE11 3TU,LEICS,ENGLAND
[2] GLAXO WELLCOME RES & DEV LTD,MED RES CTR,STEVENAGE SG1 2NY,HERTS,ENGLAND
[3] SMITHKLINE BEECHAM PHARMACEUT,EPSOM KT18 5XQ,SURREY,ENGLAND
[4] SMITHKLINE BEECHAM PHARMACEUT,BETCHWORTH RH3 7AL,SURREY,ENGLAND
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1996年 / 24期
关键词
D O I
10.1039/p19960002879
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Rhodium(II) acetate-catalysed decomposition of diazophenylacetates 1 and 3 in the presence of a range of N-H compounds results in an N-H insertion reaction of the intermediate carbenoids and formation of N-substituted phenylglycine derivatives 2 and 4. The corresponding reactions of dimethyl alpha-diazobenzylphosphonate 5 constitute a simple route to aminophosphonates 6.
引用
收藏
页码:2879 / 2884
页数:6
相关论文
共 82 条
[11]   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
[12]   ALKYLATION OF CHIRAL PHOSPHONOGLYCINE EQUIVALENTS - ASYMMETRIC-SYNTHESIS OF DIETHYL ALPHA-AMINO-ALPHA-ALKYL-PHOSPHONATES [J].
CABELLA, G ;
JOMMI, G ;
PAGLIARIN, R ;
SELLO, G ;
SISTI, M .
TETRAHEDRON, 1995, 51 (06) :1817-1826
[13]  
CAMA LD, 1978, TETRAHEDRON LETT, V44, P4233
[14]   SYNTHESIS OF 4-ARYL-3,5-BIS(ALKOXYCARBONYL)-1,4-DIHYDROPYRAZINES [J].
CHORVAT, RJ ;
RORIG, KJ .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (24) :5779-5781
[15]   Asymmetric synthesis of alpha-aminophosphonates via diastereoselective addition of phosphite to chiral imine derivatives [J].
Chung, SK ;
Kang, DH .
TETRAHEDRON-ASYMMETRY, 1996, 7 (01) :21-24
[16]   SYNTHESIS OF ALPHA-PHOSPHORYLATED CYCLOPENTANONES BY INTRAMOLECULAR CARBENOID CYCLIZATIONS OF ALPHA-DIAZO BETA-KETO ALKYLPHOSPHONATES AND PHOSPHINE OXIDES [J].
CORBEL, B ;
HERNOT, D ;
HAELTERS, JP ;
STURTZ, G .
TETRAHEDRON LETTERS, 1987, 28 (52) :6605-6608
[17]   A CONVENIENT SYNTHETIC ROUTE TO N-ARYL AND N-ALKYLAMINO(ALKYL) PHOSPHONATES AND PHOSPHINE OXIDES [J].
COUTURE, A ;
DENIAU, E ;
WOISEL, P ;
GRANDCLAUDON, P .
TETRAHEDRON LETTERS, 1995, 36 (14) :2483-2486
[18]   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
[19]   A simple synthesis of 1-aminophosphonic acids from 1-hydroxyiminophosphonates with NaBH4 in the presence of transition metal compounds [J].
Demir, AS ;
Tanyeli, C ;
Sesenoglu, O ;
Demic, S ;
Evin, OO .
TETRAHEDRON LETTERS, 1996, 37 (03) :407-410
[20]   ASYMMETRIC ELECTROPHILIC AMINATION OF CHIRAL PHOSPHORUS-STABILIZED ANIONS [J].
DENMARK, SE ;
CHATANI, N ;
PANSARE, SV .
TETRAHEDRON, 1992, 48 (11) :2191-2208