Intermolecular 1,3-dipolar cycloaddition of chiral and geometry fixed alpha-alkoxycarbonylnitrone, 5,6-dihydro-5-phenyl-2H-1,4-oxazin-2-one N-oxide

被引：36

作者：

Tamura, O

Gotanda, K

Terashima, R

Kikuchi, M

Miyawaki, T

Sakamoto, M

机构：

来源：

CHEMICAL COMMUNICATIONS | 1996年 / 16期

关键词：

D O I：

10.1039/cc9960001861

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The 1,3-dipolar cycloaddition of (R)-5,6-dihydro-5-phenyl-2H-1,4-oxazin-2-one N-oxide[(5R)-2], a chiral and geometry fixed alpha-alkoxycarbonylnitrone, with alkenes 3-6 proceeded smoothly to afford cycloadducts 7-10 as main products via beta-exo mode.

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页码：1861 / 1862

页数：2

相关论文

共 20 条

[1] THE REACTIVITIES OF SOME CYCLIC NITRONES IN 1,3-DIPOLAR CYCLOADDITION REACTIONS [J].

ALI, SA ;

WAZEER, MIM .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1986, (11) :1789-1792

[2] AROMATIC SOLVENT-INDUCED SHIFTS IN THE H-1-NMR SPECTRA OF NITRONES [J].

AURICH, HG ;

FRANZKE, M ;

KESSELHEIM, HP .

TETRAHEDRON, 1992, 48 (04) :663-668

[3] CYCLO-ADDITION OF CHIRAL NITRONES - ASYMMETRIC SYNTHESIS OF ISOXAZOLIDINES [J].

BELZECKI, C ;

PANFIL, I .

JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (08) :1212-1218

[4]

Carruthers W., 1990, CYCLOADDITION REACTI, P269

[5]

CONFALONE PN, 1988, ORG REACTIONS, V36, P1

[6] A SHORT-STEP SYNTHESIS OF 4-HYDROXYPROLINE [J].

HARA, J ;

INOUYE, Y ;

KAKISAWA, H .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1981, 54 (12) :3871-3872

[7] ENANTIOCONTROLLED CONSTRUCTION OF BICYCLIC PROLINE DERIVATIVES VIA ONE-POT GENERATION AND INTRAMOLECULAR TRAPPING OF CHIRAL STABILIZED AZOMETHINE YLIDS [J].

HARWOOD, LM ;

LILLEY, IA .

TETRAHEDRON LETTERS, 1993, 34 (03) :537-540

[8] ENANTIOSELECTIVE TOTAL SYNTHESIS OF (+)-NEGAMYCIN AND (-)-EPINEGAMYCIN BY AN ASYMMETRIC 1,3-DIPOLAR CYCLOADDITION [J].

IIDA, H ;

KASAHARA, K ;

KIBAYASHI, C .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (15) :4647-4648

[9] THE CONFIGURATIONS OF N-METHYL-BUTYL-ALPHA-METHOXYCARBONYLMETHANIMINE AND N-TERT-BUTYL-ALPHA-METHOXYCARBONYLMETHANIMINE N-OXIDES [J].

INOUYE, Y ;

TAKAYA, K ;

KAKISAWA, H .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1983, 56 (11) :3541-3542

[10] NOVEL E-Z EQUILIBRIUM OF "N-ALKYL-ALPHA-ALKOXYCARBONYLNITRONE IN SOLUTION [J].

INOUYE, Y ;

HARA, J ;

KAKISAWA, H .

CHEMISTRY LETTERS, 1980, (11) :1407-1410