title: Domino [4 + 1]-annulation of α,β-unsaturated δ-amino esters with Rh(II)-carbenoids – a new approach towards multi-functionalized N-aryl pyrrolidines.
abstract: Catalytic decomposition of diazomalonates and other diazoesters using Rh(II)- and Cu(II)-complexes in the presence of α,β-unsaturated δ-(N-aryl)amino esters gives rise to the formation of multi-functionalized pyrrolidines with yields of up to 82%. The reaction apparently occurs as a domino process involving the initial N-ylide formation followed by intramolecular Michael addition to the conjugated system of amino esters to afford the pyrrolidine heterocycle. The whole process can also be classified as a [4 + 1]-annulation of the δ-amino α,β-unsaturated ester with the carbenoid intermediate.
authors.affiliation: Saint-Petersburg State University, University Prosp. 26, St.-Petersburg 198504, Russia. valerij.nikolaev@gmail.com.
authors.forename: J J
authors.initials: JJ
authors.lastname: Medvedev
authors.forename: O S
authors.initials: OS
authors.lastname: Galkina
authors.forename: A A
authors.initials: AA
authors.lastname: Klinkova
authors.forename: D S
authors.initials: DS
authors.lastname: Giera
authors.forename: L
authors.initials: L
authors.lastname: Hennig
authors.forename: C
authors.initials: C
authors.lastname: Schneider
authors.forename: V A
authors.initials: VA
authors.lastname: Nikolaev
mesh_terms: D000596:Amino Acids / Q000737:chemistry*; D003500:Cyclization; D004952:Esters / Q000737:chemistry*; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry; D012238:Rhodium / Q000737:chemistry*
chemical_list: D000596:Amino Acids; D004952:Esters; D009942:Organometallic Compounds; D011759:Pyrrolidines; C030011:carbene; D012238:Rhodium; D008697:Methane