title: Enantioselective organocatalytic one-pot amination/aza-Michael/aldol condensation reaction sequence: synthesis of 3-pyrrolines with a quaternary stereocenter.
abstract: Primary amine-catalyzed direct conversion of α,α-disubstituted aldehydes into 3-pyrrolines with a quaternary stereocenter is reported. The one-pot enantioselective sequence is based on a α-amination, an aza-Michael addition of hydrazine, an aldol condensation dehydratation and proceeds with good yields and excellent levels of enantioselectivity. Synthetically attractive applications including the formation of aziridinopyrrolidine or epoxypyrrolidine derivatives with good yields and selectivities are also described.
authors.affiliation: Institut Lavoisier de Versailles, UMR CNRS 8180, Université de Versailles Saint-Quentin-en-Yvelines, 45, Avenue des Etats-unis, 78035 Versailles Cedex, France.
authors.forename: Alaric
authors.initials: A
authors.lastname: Desmarchelier
authors.forename: Vincent
authors.initials: V
authors.lastname: Coeffard
authors.forename: Xavier
authors.initials: X
authors.lastname: Moreau
authors.forename: Christine
authors.initials: C
authors.lastname: Greck
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D000586:Amination; D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D006834:Hydrazines / Q000737:chemistry*; D015394:Molecular Structure; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D000588:Amines; D006834:Hydrazines; D011758:Pyrroles; C029424:hydrazine; C013231:pyrroline