4-Nitroisoxazoles as nitroalkene heterodienes: diastereoselective synthesis of spiro tricyclic nitroso acetals by thermal reactions with ethyl vinyl ether

被引：14

作者：

Giomi, D ^{[1
]}

Turchi, S ^{[1
]}

Danesi, A ^{[1
]}

Faggi, C ^{[1
]}

机构：

[1] Univ Florence, Dpto Chim Organ Ugo Schiff, Ctr Studio, CNR, I-50121 Florence, Italy

来源：

TETRAHEDRON | 2001年 / 57卷 / 19期

关键词：

cycloadditions; 4-nitroisoxazoles; nitroalkene heterodienes; spiro nitroso acetals;

D O I：

10.1016/S0040-4020(01)00310-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A few 4-nitroisoxazoles were found to undergo highly diastereoselective pericyclic homodomino processes with the title enol ether affording 1,6,9-trioxa-5,9a-diazacyclopenta[d]indenes through bicyclic nitronates as hey intermediates. Formation of isoxazolooxepine systems is also reported together with a domino reaction with the above reagent and methyl acrylate. Two X-ray analyses of compounds 8 and 13 were carried out to firmly establish their stereochemistry. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：4237 / 4242

页数：6

共 38 条

[1] SIR92 - a program for automatic solution of crystal structures by direct methods [J].

ALTOMARE, A ;

CASCARANO, G ;

GIACOVAZZO, G ;

GUAGLIARDI, A ;

BURLA, MC ;

POLIDORI, G ;

CAMALLI, M .

JOURNAL OF APPLIED CRYSTALLOGRAPHY, 1994, 27 :435-435

[2] Substrate-controlled stereodifferentiation of tandem [4+2]/[3+2] cycloadditions by a vicinal carbohydrate-based template [J].

Avalos, M ;

Babiano, R ;

Cintas, P ;

Higes, FJ ;

Jimenez, JL ;

Palacios, JC ;

Silva, MA .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (05) :1880-1882

[3] CONJUGATED NITROALKENES - VERSATILE INTERMEDIATES IN ORGANIC-SYNTHESIS [J].

BARRETT, AGM ;

GRABOSKI, GG .

CHEMICAL REVIEWS, 1986, 86 (05) :751-762

[4] Tandem inter[4+2]/intra[3+2]cycloaddition of nitroalkenes. 23. Tandem cycloaddition chemistry of nitroalkenes: Probing the remarkable stereochemical influence of the Lewis acid [J].

Denmark, SE ;

Seierstad, M .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (05) :1610-1619

[5] Tandem cycloaddition chemistry of nitroalkenes: Preparative and theoretical studies on the stereochemical course of [3+2] cycloaddition of cyclic nitronates [J].

Denmark, SE ;

Seierstad, M ;

Herbert, B .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (03) :884-901

[6] INTERMOLECULAR [4 + 2]-CYCLOADDITIONS OF NITROALKENES WITH CYCLIC OLEFINS - TRANSFORMATIONS OF CYCLIC NITRONATES [J].

DENMARK, SE ;

CRAMER, CJ ;

STERNBERG, JA .

HELVETICA CHIMICA ACTA, 1986, 69 (08) :1971-1989

[7] Tandem inter [4+2] intra [3+2] cycloadditions of nitroalkenes.: The bridged mode (β-tether) [J].

Denmark, SE ;

Dixon, JA .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (18) :6167-6177

[8] Tandem [4+2]/[3+2] cycloadditions of nitroalkenes .9. Synthesis of (-)-rosmarinecine [J].

Denmark, SE ;

Thorarensen, A ;

Middleton, DS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (35) :8266-8277

[9] Tandem [4+2]/[3+2]cycloadditions of nitroalkenes .11. The synthesis of (+)-crotanecine [J].

Denmark, SE ;

Thorarensen, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (01) :125-137

[10] Tandem [4+2]/[3+2] cycloadditions of nitroalkenes .13. The synthesis of (-)-detoxinine [J].

Denmark, SE ;

Hurd, AR ;

Sacha, HJ .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (06) :1668-1674

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