Synthesis of chiral pyridino-15-crown-5 type ligands containing α-D-hexapyranoside unit and their application in asymmetric synthesis

被引：13

作者：

Mako, Attila ^{[1
]}

Bako, Peter ^{[1
]}

Szoellosy, Aron ^{[2
]}

Bako, Tibor ^{[3
]}

Peltz, Csaba ^{[3
]}

Keglevich, Peter ^{[1
]}

机构：

[1] Budapest Univ Technol & Econ, Dept Organ Chem & Technol, POB 91, H-1521 Budapest, Hungary

[2] Dept Gen & Analyt Chem, H-1525 Budapest, Hungary

[3] EGIS Pharmaceut PLC, Spectroscop Dept, H-1475 Budapest, Hungary

来源：

ARKIVOC | 2009年

关键词：

Asymmetric catalysis; crown compounds; ring closure; phase-transfer catalysis; Michael addition; HOST-GUEST COMPLEXATION; CROWN-ETHERS; AZACROWN ETHERS; D-GLUCOSE; MICHAEL-ADDITION; ENANTIOMERIC RECOGNITION; AMINE; SALTS; ENANTIOSEPARATION; 2-NITROPROPANE;

D O I：

10.3998/ark.5550190.0010.716

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of novel chiral monoaza-15-crown-5 compounds (1-4) with pyridine-ring starting from methyl-4,6-O-benzylidene-alpha-D-glucopyranoside and methyl-4,6-O-benzylidene-alpha-D-mannopyranoside by different methods are reported. These crown ethers showed significant asymmetric induction in a Michael addition (up to 80% ee).

引用

页码：165 / 179

页数：15

共 39 条

[31]

O'Donnell M.J., 2000, CATALYTIC ASYMMETRIC, V2nd, P727

[32] SYNTHESIS OF CHIRAL DIAZA CROWN ETHERS INCORPORATING CARBOHYDRATE UNITS [J].

PIETRASZKIEWICZ, M ;

JURCZAK, J .

TETRAHEDRON, 1984, 40 (15) :2967-2970

[33] Enantiomerically pure chiral pyridino-crown ethers:: synthesis and enantioselectivity toward the enantiomers of α-(1-naphthyl)ethylammonium perchlorate [J].

Samu, E ;

Huszthy, P ;

Horváth, G ;

Szöllosy, A ;

Neszmélyi, A .

TETRAHEDRON-ASYMMETRY, 1999, 10 (18) :3615-3626

[34] A NEW TYPE OF FUNCTIONALIZED CRYPTAND-LIKE IONOPHORE - SYNTHESIS, STRUCTURE AND COMPLEXATION [J].

STIBOR, I ;

HOLY, P ;

ZAVADA, J ;

KOUDELKA, J ;

NOVAK, J ;

ZAJICEK, J ;

BELOHRADSKY, M .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (22) :1581-1583

[35] CHIRAL CROWN ETHERS [J].

STODDART, JF .

TOPICS IN STEREOCHEMISTRY, 1987, 17 :207-288

[36] Asymmetric Michael addition and deracemization of enolate by chiral crown ether [J].

Töke, L ;

Bakó, P ;

Keseru, GM ;

Albert, M ;

Fenichel, L .

TETRAHEDRON, 1998, 54 (1-2) :213-222

[37] LI+ ION-SELECTIVE BINDING AND TRANSPORT-PROPERTIES OF 12-MEMBERED RING LARIAT ETHERS - EXPERIMENTAL AND COMPUTATIONAL STUDIES ON CROWN RING SIDEARM COOPERATIVITY [J].

TSUKUBE, H ;

INOUE, T ;

HORI, K .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (26) :8047-8052

[38] SYNTHESIS OF CARBOHYDRATE CONTAINING CROWN ETHERS AND THEIR APPLICATION AS CATALYSTS IN ASYMMETRIC MICHAEL ADDITIONS [J].

VANMAARSCHALKERWAART, DAH ;

WILLARD, NP ;

PANDIT, UK .

TETRAHEDRON, 1992, 48 (40) :8825-8840

[39] Enantiomeric recognition of amine compounds by chiral macrocyclic receptors [J].

Zhang, XX ;

Bradshaw, JS ;

Izatt, RM .

CHEMICAL REVIEWS, 1997, 97 (08) :3313-3361

← 1 2 3 4 →