One-pot synthesis of α-aminophosphonates catalyzed by antimony trichloride adsorbed on alumina

被引：99

作者：

Ambica ^{[1
]}

Kumar, Satish ^{[1
]}

Taneja, Subhash C. ^{[2
]}

Hundal, Maninder S. ^{[3
]}

Kapoor, Kamal K. ^{[1
]}

机构：

[1] Univ Jammu, Dept Chem, Jammu 180006, India

[2] Indian Inst Integrat Med, Bioorgan Chem Div, Jammu 180001, India

[3] Guru Nanak Dev Univ, Dept Chem, Amritsar 143005, Punjab, India

来源：

TETRAHEDRON LETTERS | 2008年 / 49卷 / 14期

关键词：

sbCl(3)/Al2O3; alpha-amino acid; alpha-aminophosphonate; solid supported reagents; recyclability;

D O I：

10.1016/j.tetlet.2008.02.047

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

SbCl3 adsorbed on Al2O3 is found to be an efficient and recyclable catalyst in promoting three-component coupling reactions of aldehydes (aromatic and aliphatic), amines (aryl amines, aliphatic amines and esters of S-cc-amino acids) and dialkylphosphites to afford the corresponding alpha-aminophosphonates in high yields. The ethyl ester of S-phenylalanine was observed to yield the corresponding ot-aminophosphonate with S,S-diastereoisomer formed in dominance over the S,R-diastereoisomer. (C) 2008 Elsevier Ltd. All rights reserved.

引用

收藏

页码：2208 / 2212

页数：5

相关论文

共 34 条

[1] Bronsted acid-mediated synthesis of α-amino phosphonates under solvent-free conditions [J].

Akiyama, T ;

Sanada, M ;

Fuchibe, K .

SYNLETT, 2003, (10) :1463-1464

[2] PHOSPHONOPEPTIDES, A NEW CLASS OF SYNTHETIC ANTIBACTERIAL AGENTS [J].

ALLEN, JG ;

ATHERTON, FR ;

HALL, MJ ;

HASSALL, CH ;

HOLMES, SW ;

LAMBERT, RW ;

NISBET, LJ ;

RINGROSE, PS .

NATURE, 1978, 272 (5648) :56-58

[3] 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

[4]

[Anonymous], J CHEM SOC P1, DOI [DOI 10.1039/P19840002845, 10.1039/P19840002845]

[5]

[Anonymous], 1988, ALDRICHIM ACTA

[6] 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

[7] Lithium perchlorate-catalyzed three-component coupling:: A facile and general method for the synthesis of α-aminophosphonates under solvent-free conditions [J].

Azizi, N ;

Saidi, MR .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (23) :4630-4633

[8] An extremely efficient three-component reaction of aldehydes/ketones, amines, and phosphites (Kabachnik-Fields reaction) for the synthesis of α-aminophosphonates catalyzed by magnesium perchlorate [J].

Bhagat, Srikant ;

Chakraborti, Asit K. .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (04) :1263-1270

[9] Three component coupling catalyzed by TaCl5-SiO2:: synthesis of α-amino phosphonates [J].

Chandrasekhar, S ;

Prakash, SJ ;

Jagadeshwar, V ;

Narsihmulu, C .

TETRAHEDRON LETTERS, 2001, 42 (32) :5561-5563

[10] Development of the Ti-catalyzed intermolecular hydroamination of alkynes [J].

Doye, S .

SYNLETT, 2004, (10) :1653-1672

← 1 2 3 4 →