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.
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页码：2879 / 2884
页数：6
相关论文
共 82 条
[1]   An efficient route to the alpha-methyl ester of L-glutamic acid, and its conversion into cis-5-hydroxy-L-pipecolic acid [J].
Adams, DR ;
Bailey, PD ;
Collier, ID ;
Heffernan, JD ;
Stokes, S .
CHEMICAL COMMUNICATIONS, 1996, (03) :349-350
[2]   RHODIUM (II) CATALYZED-REACTIONS OF DIAZO-CARBONYL COMPOUNDS [J].
ADAMS, J ;
SPERO, DM .
TETRAHEDRON, 1991, 47 (10-11) :1765-1808
[3]   DIASTEREOSELECTIVITY IN THE O-H INSERTION REACTIONS OF RHODIUM CARBENOIDS DERIVED FROM PHENYLDIAZOACETATES OF CHIRAL ALCOHOLS - PREPARATION OF ALPHA-HYDROXY AND ALPHA-ALKOXY ESTERS [J].
ALLER, E ;
BROWN, DS ;
COX, GG ;
MILLER, DJ ;
MOODY, CJ .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (14) :4449-4460
[4]   BETA-LACTAMS FROM ESTER ENOLATES AND SILYLIMINES - ENANTIOSELECTIVE SYNTHESIS OF THE TRANS-CARBAPENEM ANTIBIOTICS (+)-PS-5 AND (+)-PS-6 [J].
ANDREOLI, P ;
CAINELLI, G ;
PANUNZIO, M ;
BANDINI, E ;
MARTELLI, G ;
SPUNTA, G .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (21) :5984-5990
[5]   SYNTHESIS OF 3-METHYLPHOSPHONYL THIENAMYCIN AND RELATED 3-PHOSPHONYL CARBAPENEMS [J].
ANDRUS, A ;
CHRISTENSEN, BG ;
HECK, JV .
TETRAHEDRON LETTERS, 1984, 25 (06) :595-598
[6]   ALPHA-AMINOPHOSPHONATE DERIVATIVES AS NUCLEOPHILES IN DIASTEREOSELECTIVE AND ENANTIOSELECTIVE PALLADIUM-CATALYZED ALLYLIC SUBSTITUTION-REACTIONS [J].
BALDWIN, IC ;
WILLIAMS, JMJ ;
BECKETT, RP .
TETRAHEDRON-ASYMMETRY, 1995, 6 (03) :679-682
[7]   A NOVEL ENTRY TO CARBENOID SPECIES VIA BETA-KETOSULFOXONIUM YLIDES [J].
BALDWIN, JE ;
ADLINGTON, RM ;
GODFREY, CRA ;
GOLLINS, DW ;
VAUGHAN, JG .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (18) :1434-1435
[8]  
BARTELS G, 1980, LIEBIGS ANN CHEM, P168
[9]  
BLADES CE, 1956, J ORG CHEM, V21, P1013
[10]   SYNTHESIS OF A 4-BETA-CARBOXYETHYL DERIVATIVE OF THIENAMYCIN [J].
BOUTHILLIER, G ;
MASTALERZ, H ;
MENARD, M .
TETRAHEDRON LETTERS, 1994, 35 (27) :4689-4692
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