A PRACTICAL SYNTHESIS OF ALPHA-AMINOPHOSPHONIC ACIDS

被引：69

作者：

GENET, JP

UZIEL, J

PORT, M

TOUZIN, AM

ROLAND, S

THORIMBERT, S

TANIER, S

机构：

[1] Laboratoire de Synthèse Organique, associé au CNRS.Ecole Nationale Supérieure de Chimie de Paris, 75231 Paris Cedex 05, 11, rue Pierre et Marie Curie

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 01期

关键词：

SCHIFF BASES OF DITERBUTYLAMINOMETHYLPHOSPHONATE; PHASE TRANSFERT CATALYSIS; PALLADIUM-CATALYZED ALLYLIC SUBSTITUTION; MICHAEL ADDITIONS;

D O I：

10.1016/S0040-4039(00)77677-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The preparation of diterbutyl-N (diphenylmethylene) aminomethylphosphonate 3 in four steps (42% overall yield) from N-hydroxymethyl phtalimide 1 is described. Various alpha-substituted alpha-aminophosphonic acids 5 containing functionalized unsaturated chains have been synthesized by alkylation of 3 under phase transfer catalysis with halides, Michael acceptors and palladium promoted reactions, followed by mild hydrolysis.

引用

页码：77 / 80

页数：4

共 23 条

[1] CONVERSION OF ALPHA-AMINOCARBOXYLIC ACIDS TO ALPHA-AMINOPHOSPHONIC ACIDS
CORCORAN, RC
GREEN, JM
[J]. TETRAHEDRON LETTERS, 1990, 31 (47) : 6827 - 6830
[2] Davidsen S. K., 1987, ORG SYNTH, V65, P119
[3] DEHNEL A, 1978, B SOC CHIM FR, V2, P95
[4] SYNTHESIS OF ALPHA-AMINO-ACIDS BY CATALYTIC PALLADIUM (O) ALKYLATION OF SCHIFF-BASES
FERROUD, D
GENET, JP
KIOLLE, R
[J]. TETRAHEDRON LETTERS, 1986, 27 (01) : 23 - 26
[5] FERROUD D, 1986, TETRAHEDRON LETT, V27, P4573
[6] GENET JP, 1990, SYNTHESIS-STUTTGART, P41
[7] SYNTHESIS OF ALPHA-AMINO-ACIDS USING TRANSITION-METAL CATALYSIS-ALKYLATION OF SCHIFF-BASES DERIVED FROM ALPHA - AMINO-ACID ESTERS (REGIO, STEREO - SELECTIVITY
GENET, JP
JUGE, S
ACHI, S
MALLART, S
MONTES, JR
LEVIF, G
[J]. TETRAHEDRON, 1988, 44 (17) : 5263 - 5275
[8] ENANTIOSELECTIVITY IN ORGANO TRANSITION-METAL CHEMISTRY - AN UNPRECEDENTED LIGAND EFFECT IN PI-ALLYL PALLADIUM CHEMISTRY
GENET, JP
JUGE, S
MONTES, JR
GAUDIN, JM
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (11) : 718 - 719
[9] SYNTHESIS OF ALPHA-AMINOPHOSPHONIC ACIDS BY PD(0) ALKYLATION OF DIETHYL AMINOMETHYLPHOSPHONATE SCHIFF-BASES
GENET, JP
UZIEL, J
JUGE, S
[J]. TETRAHEDRON LETTERS, 1988, 29 (36) : 4559 - 4562
[10] A VERSATILE ASYMMETRIC-SYNTHESIS OF ALPHA-AMINO ALPHA-ALKYL-PHOSPHONIC ACIDS OF HIGH ENANTIOMERIC PURITY
HANESSIAN, S
BENNANI, YL
[J]. TETRAHEDRON LETTERS, 1990, 31 (45) : 6465 - 6468

← 1 2 3 →