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  • Title: Investigation of Lewis acid-catalyzed asymmetric aza-Diels-Alder reactions of 2H-azirines.
    Author: Timén AS, Somfai P.
    Journal: J Org Chem; 2003 Dec 26; 68(26):9958-63. PubMed ID: 14682688.
    Abstract:
    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.
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