Investigation of Lewis acid-catalyzed asymmetric aza-Diels-Alder reactions of 2H-azirines.
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.
Timén
Asa Sjöholm
AS
Department of Chemistry, Organic Chemistry, Royal Institute of Technology (KTH), SE-100 44 Stockholm, Sweden.
Somfai
Peter
P
D001389:Azirines / Q000737:chemistry*; D002384:Catalysis; D003517:Cyclopentanes / Q000737:chemistry; D006863:Hydrogen-Ion Concentration; D011725:Pyridines / Q000138:chemical synthesis; D013237:Stereoisomerism
D001389:Azirines; D003517:Cyclopentanes; D011725:Pyridines