title: A formal [3 + 3] cycloaddition reaction. 5. An enantioselective intramolecular formal aza-[3 + 3] cycloaddition reaction promoted by chiral amine salts.
abstract: A detailed account on chiral secondary amine salt promoted enantioselective intramolecular formal aza-[3 + 3] cycloadditions is described here for the first time. The dependence of enantioselectivity on the structural feature of these chiral amines is thoroughly investigated. This study also reveals a very interesting reversal of the stereochemistry in the respective cycloadducts obtained using C(1)- and C(2)-symmetric amine salts. In addition, the influence of solvents, counteranions, and temperatures on the enantioselectivity is described, and a unified mechanistic model based on experimental results as well as semiempirical calculations is proposed.
authors.affiliation: Department of Chemistry, University of Minnesota, Minneapolis, MN 55455, USA.
authors.forename: Aleksey I
authors.initials: AI
authors.lastname: Gerasyuto
authors.forename: Richard P
authors.initials: RP
authors.lastname: Hsung
authors.forename: Nadiya
authors.initials: N
authors.lastname: Sydorenko
authors.forename: Brian
authors.initials: B
authors.lastname: Slafer
mesh_terms: D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D018360:Crystallography, X-Ray; D003500:Cyclization; D006571:Heterocyclic Compounds / Q000138:chemical synthesis*; D008956:Models, Chemical; D008968:Molecular Conformation; D015394:Molecular Structure; D012492:Salts / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000588:Amines; D006571:Heterocyclic Compounds; D012492:Salts