Asymmetric synthesis of alpha-aminophosphonates via diastereoselective addition of phosphite to chiral imine derivatives

被引：58

作者：

Chung, SK

Kang, DH

机构：

[1] Department of Chemistry, Pohang Univ. of Sci. and Technology, Pohang

来源：

TETRAHEDRON-ASYMMETRY | 1996年 / 7卷 / 01期

关键词：

D O I：

10.1016/0957-4166(95)00411-4

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

One pot three component reactions employing homochiral (1S)-(+)-camphorsulfon-amide-derived carbamate, aldehydes and diethyl phosphite at 0 degrees C was found to give protected (S)-alpha-aminophosphonates in high enantiomeric purities.

引用

页码：21 / 24

页数：4

共 42 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]

BAJUSZ S, 1989, FEBS LETT, V117, P308

[4] DIASTEREOSELECTIVITY IN THE ALKYLATION OF CHIRAL 2-AMINOMETHYL-1,3,2-DIOXAPHOSPHORINANE 2-OXIDES [J].

BARTLETT, PA ;

MCLAREN, KL .

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1987, 33 (1-2) :1-14

[5] SYNTHESIS OF (1S,2S)-PHOSPHOTHREONINE VIA N-TRIMETHYLSILYLIMINE OF (S)-LACTIC ALDEHYDE [J].

BONGINI, A ;

CAMERINI, R ;

HOFMAN, S ;

PANUNZIO, M .

TETRAHEDRON LETTERS, 1994, 35 (43) :8045-8048

[6] 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

[7] NUCLEAR MAGNETIC-RESONANCE ENANTIOMER REAGENTS - CONFIGURATIONAL CORRELATIONS VIA NUCLEAR MAGNETIC-RESONANCE CHEMICAL-SHIFTS OF DIASTEREOMERIC MANDELATE, O-METHYLMANDELATE, AND ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETATE (MTPA) ESTERS [J].

DALE, JA ;

MOSHER, HS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (02) :512-519

[8] ASYMMETRIC ELECTROPHILIC AMINATION OF CHIRAL PHOSPHORUS-STABILIZED ANIONS [J].

DENMARK, SE ;

CHATANI, N ;

PANSARE, SV .

TETRAHEDRON, 1992, 48 (11) :2191-2208

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

DHAWAN, B ;

REDMORE, D .

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

[10]

EVANS DA, 1989, ORG SYNTH, V68, P77

← 1 2 3 4 5 →