Asymmetric Synthesis of Substituted α-Amino Phosphonates with Chiral Crown Ethers as Catalysts

被引：30

作者：

Jaszay, Zsuzsa ^{[1
]}

Pham, Truong Son ^{[1
]}

Nemeth, Gabriella ^{[1
]}

Bako, Peter ^{[1
]}

Petnehazy, Imre ^{[1
]}

Toke, Laszlo ^{[1
]}

机构：

[1] Budapest Univ Technol & Econ, Dept Organ Chem & Technol, H-1521 Budapest, Hungary

来源：

SYNLETT | 2009年 / 09期

基金：

匈牙利科学研究基金会;

关键词：

Michael additions; asymmetric catalysis; chiral phase-transfer catalysis; chiral crown compounds; aminophosphonates; ENANTIOSELECTIVE MICHAEL ADDITION; AMINOPHOSPHONIC ACIDS; D-GLUCOSE; ENANTIOPURE SULFINIMINES; DERIVATIVES; COMPLEXES; BOND; HYDROPHOSPHONYLATION; 2-NITROPROPANE; SPECIFICITY;

D O I：

10.1055/s-0029-1217166

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple, phase-transfer catalytic synthesis of enantioenriched phosphonoglutaminic acid derivatives (ee Lip to 86%) has been developed by using 'sugar-based' crown ether catalysts.

引用

页码：1429 / 1432

页数：4

共 28 条

[1] INHIBITION OF HUMAN IMMUNODEFICIENCY VIRUS-1 PROTEASE BY A C2-SYMMETRICAL PHOSPHINATE - SYNTHESIS AND CRYSTALLOGRAPHIC ANALYSIS [J].

ABDELMEGUID, SS ;

ZHAO, BG ;

MURTHY, KHM ;

WINBORNE, E ;

CHOI, JK ;

DESJARLAIS, RL ;

MINNICH, MD ;

CULP, JS ;

DEBOUCK, C ;

TOMASZEK, TA ;

MEEK, TD ;

DREYER, GB .

BIOCHEMISTRY, 1993, 32 (31) :7972-7980

[2] 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

[3] ASYMMETRIC MICHAEL REACTION USING MACROCYCLIC LACTOSE DERIVATIVES AS CHIRAL CATALYSTS [J].

ALONSOLOPEZ, M ;

MARTINLOMAS, M ;

PENADES, S .

TETRAHEDRON LETTERS, 1986, 27 (30) :3551-3554

[4] 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

[5]

Bako P, 1997, SYNLETT, P291

[6] Enantioselective Michael addition of 2-nitropropane to chalcone analogues catalyzed by chiral azacrown ethers based on α-D-glucose and D-mannitol [J].

Bakó, T ;

Bakó, P ;

Keglevich, G ;

Báthori, N ;

Czugler, M ;

Tatai, J ;

Novák, T ;

Parlagh, G ;

Toke, L .

TETRAHEDRON-ASYMMETRY, 2003, 14 (13) :1917-1923

[7] Enantioselective Michael reaction of 2-nitropropane with substituted chalcones catalysed by chiral azacrown ethers derived from α-D-glucose [J].

Bakó, T ;

Bakó, P ;

Szöllosy, A ;

Czugler, M ;

Keglevich, G ;

Toke, L .

TETRAHEDRON-ASYMMETRY, 2002, 13 (02) :203-209

[8] Asymmetric synthesis of quaternary α-amino phosphonates using sulfinimines [J].

Davis, FA ;

Lee, S ;

Yan, HX ;

Titus, DD .

ORGANIC LETTERS, 2001, 3 (11) :1757-1760

[9]

GROTH U, 1992, LIEBIGS ANN CHEM, P903

[10] Catalytic enantioselective Michael addition in the synthesis of α-aminophosphonates [J].

Jászay, ZM ;

Németh, G ;

Pham, TS ;

Petneházy, I ;

Grün, A ;

Toke, L .

TETRAHEDRON-ASYMMETRY, 2005, 16 (23) :3837-3840

← 1 2 3 →