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Investigation of Lewis acid-catalyzed asymmetric aza-Diels-Alder reactions of 2H-azirines
KTH, Superseded Departments, Chemistry.
2003 (English)In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 68, no 26, 9958-9963 p.Article in journal (Refereed) Published
Abstract [en]

Asymmetric Diels-Alder reactions with 2H-azirines as dienophiles have been studied. Diastereoselective reactions with an enantiopure azirine 1b, bearing a chiral auxiliary, gave substituted bi-and tricyclic tetrahydropyridines in high yield and stereoselectivity, under the influence of a Lewis acid. The novel enantioselective [4+2] cycloaddition reaction of 3-benzyl-2H-azirine carboxylate with cyclopentadiene was investigated with various chiral Lewis acid complexes and provided the corresponding tetrahydropyridines in moderate to low yield and enantioselectivity.

Place, publisher, year, edition, pages
2003. Vol. 68, no 26, 9958-9963 p.
Keyword [en]
benzyl 2h-azirine-3-carboxylate, cycloadditions, dienophiles, aziridines
URN: urn:nbn:se:kth:diva-23038DOI: 10.1021/jo0352326ISI: 000187427500011OAI: diva2:341736
QC 20100525Available from: 2010-08-10 Created: 2010-08-10Bibliographically approved

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Somfai, Peter
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