ASYMMETRIC-SYNTHESIS OF DIETHYL ALPHA-AMINO-ALPHA-ALKYL-PHOSPHONATES BY ALKYLATION OF THE CHIRAL SCHIFF-BASE DERIVED FROM (+)-KETOPINIC ACID AND DIETHYLAMINOMETHYL PHOSPHONATE

被引：29

作者：

FERRARI, M ^{[1
]}

JOMMI, G ^{[1
]}

MIGLIERINI, G ^{[1
]}

PAGLIARIN, R ^{[1
]}

SISTI, M ^{[1
]}

机构：

[1] UNIV MILAN,DIPARTIMENTO CHIM ORGAN & IND,VIA VENEZIAN 21,I-20133 MILAN,ITALY

来源：

SYNTHETIC COMMUNICATIONS | 1992年 / 22卷 / 01期

关键词：

D O I：

10.1080/00397919208021082

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The alkylation of the chiral Schiff base derived from the condensation of (+)-ketopinic acid and diethyl aminomethylphosphonate followed by hydrolysis affords diethyl (S)-alpha-amino-alpha-alkyl phosphonates with high enantiomeric excesses when benzyl or allyl halides are used in the alkylation step. An improved procedure for the preparation of diethyl aminomethylphosphonate is also reported.

引用

页码：107 / 123

页数：17

共 27 条

[1] RENIN INHIBITORS - SYNTHESIS OF TRANSITION-STATE ANALOG INHIBITORS CONTAINING PHOSPHORUS-ACID DERIVATIVES AT THE SCISSILE BOND [J].

ALLEN, MC ;

FUHRER, W ;

TUCK, B ;

WADE, R ;

WOOD, JM .

JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (07) :1652-1661

[2] SYNTHESIS AND STRUCTURE-ACTIVITY-RELATIONSHIPS OF ANTIBACTERIAL PHOSPHONOPEPTIDES INCORPORATING (1-AMINOETHYL)PHOSPHONIC ACID AND (AMINOMETHYL)PHOSPHONIC ACID [J].

ATHERTON, FR ;

HASSALL, CH ;

LAMBERT, RW .

JOURNAL OF MEDICINAL CHEMISTRY, 1986, 29 (01) :29-40

[3]

BARTLETT PA, 1988, PHOSPHORUS SULFUR, V33, P1

[4] 1-AMINOALKYLPHOSPHONOUS ACIDS .1. ISOSTERES OF THE PROTEIN AMINO-ACIDS [J].

BAYLIS, EK ;

CAMPBELL, CD ;

DINGWALL, JG .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1984, (12) :2845-2853

[5]

CASELLA L, 1990, CISCI, P329

[6]

CASELLA L, 1988, TETRAHEDRON LETT, P2067

[7] ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETIC ACID, A VERSATILE REAGENT FOR DETERMINATION OF ENANTIOMERIC COMPOSITION OF ALCOHOLS AND AMINES [J].

DALE, JA ;

DULL, DL ;

MOSHER, HS .

JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (09) :2543-&

[8] OPTICALLY-ACTIVE 1-AMINOALKYLPHOSPHONIC ACIDS [J].

DHAWAN, B ;

REDMORE, D .

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1987, 32 (3-4) :119-144

[9] PHOSPHORUS AMINO-ACID-ANALOGS AS INHIBITORS OF LEUCINE AMINOPEPTIDASE [J].

GIANNOUSIS, PP ;

BARTLETT, PA .

JOURNAL OF MEDICINAL CHEMISTRY, 1987, 30 (09) :1603-1609

[10] A VERSATILE ASYMMETRIC-SYNTHESIS OF ALPHA-AMINO ALPHA-ALKYL-PHOSPHONIC ACIDS OF HIGH ENANTIOMERIC PURITY [J].

HANESSIAN, S ;

BENNANI, YL .

TETRAHEDRON LETTERS, 1990, 31 (45) :6465-6468

← 1 2 3 →