1,3-Dipolar cycloadditions of prop-1-ene-1,3-sultone with nitrile oxides/nitrones

被引：23

作者：

Zhang, H ^{[1
]}

Chan, WH ^{[1
]}

Lee, AWM ^{[1
]}

Wong, WY ^{[1
]}

机构：

[1] Hong Kong Baptist Univ, Dept Chem & Chem Lab, Inst Mol Technol Drug Discovery & Synthesis, Kowloon, Hong Kong, Peoples R China

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 02期

关键词：

D O I：

10.1016/S0040-4039(02)02502-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The scope and limitations of dipolar cycloaddition reactions between nitrile oxides nitrones and prop-1-ene-1,3-sultone have been investigated. A remarkably high degree of regioselectivity and stereoselectivity as observed. The homochiral sultam 8e was synthesized in a Four-step reaction sequence starting from the substituted isoxazoline 4e obtained from the cycloaddition. The absolute stereochemistry of this material vas assigned by an X-ray crystallographic investigation of the intermediate 7e. (C) 2002 Elsevier Science Ltd. All rights reserved.

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页码：395 / 397

页数：3

相关论文

共 21 条

[1] 1,3-dipolar cycloaddition of nitrile oxides to 2(5H)-furanones substituted at the 5-position by sulphur bearing groups [J].

Alguacil, R ;

Farina, F ;

Martin, MV .

TETRAHEDRON, 1996, 52 (10) :3457-3472

[2] STEREOCONTROLLED TOTAL SYNTHESIS OF "1-ALPHA,25-DIHYDROXYCHOLECALCIFEROL AND 1-ALPHA,25-DIHYDROXYERGOCALCIFEROL [J].

BAGGIOLINI, EG ;

IACOBELLI, JA ;

HENNESSY, BM ;

BATCHO, AD ;

SERENO, JF ;

USKOKOVIC, MR .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (16) :3098-3108

[3] CYANOHYDRIDOBORATE ANION AS A SELECTIVE REDUCING AGENT [J].

BORCH, RF ;

BERNSTEIN, MD ;

DURST, HD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (12) :2897-+

[4]

Carruthers W, 1990, Cycloaddition Reactions in Organic Synthesis

[5] New chiral sultam auxiliaries: preparation and their application in asymmetric Diels-Alder reactions [J].

Chan, WH ;

Lee, AWM ;

Jiang, LS ;

Mak, TCW .

TETRAHEDRON-ASYMMETRY, 1997, 8 (15) :2501-2504

[6] REDUCTION OF DELTA-2-ISOXAZOLINES .3. RANEY-NICKEL CATALYZED FORMATION OF BETA-HYDROXY KETONES [J].

CURRAN, DP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (18) :5826-5833

[7] 1,3-DIPOLAR CYCLOADDITION OF ENANTIOPURE GAMMA-OXYGENATED-ALPHA,BETA-UNSATURATED PHENYL SULFONES WITH NITRILE OXIDES [J].

DEBLAS, J ;

CARRETERO, JC ;

DOMINGUEZ, E .

TETRAHEDRON-ASYMMETRY, 1995, 6 (05) :1035-1038

[8]

Huisgen R., 1984, 1 3 DIPOLAR CYCLOADD, VI

[9] Synthesis and Diels-Alder reactions of prop-1-ene-1,3-sultone, and chemical transformations of the Diels-Alder adducts [J].

Jiang, LS ;

Chan, WH ;

Lee, AWM .

TETRAHEDRON, 1999, 55 (08) :2245-2262

[10] ASYMMETRIC TOTAL SYNTHESIS OF (+)-NEGAMYCIN AND (-)-3-EPINEGAMYCIN VIA ENANTIOSELECTIVE 1,3-DIPOLAR CYCLO-ADDITION [J].

KASAHARA, K ;

IIDA, H ;

KIBAYASHI, C .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (09) :2225-2233