title: Organocatalytic enantio- and diastereoselective synthesis of 3,5-disubstituted prolines.
abstract: The asymmetric synthesis of substituted pyrrolidines has been accomplished using a novel organocatalytic cyclization reaction promoted by a Cinchona alkaloid based primary amine. The reaction proceeds smoothly yielding pyrrolidine-2,2-dicarboxylates after in situ diastereoselective reduction with high levels of enantioselection. Furthermore, these adducts could be easily transformed into N-protected disubstituted prolines through the base-promoted diastereoselective C → N alkoxycarbonyl transfer reaction.
authors.affiliation: Department of Organic Chemistry II, University of the Basque Country (UPV/EHU), P.O. Box 644, 48080 Bilbao, Spain. marisa.carrillo@ehu.es joseluis.vicario@ehu.es.
authors.forename: Iker
authors.initials: I
authors.lastname: Riaño
authors.affiliation: Department of Organic Chemistry II, University of the Basque Country (UPV/EHU), P.O. Box 644, 48080 Bilbao, Spain. marisa.carrillo@ehu.es joseluis.vicario@ehu.es.
authors.forename: Estibaliz
authors.initials: E
authors.lastname: Díaz
authors.affiliation: Department of Organic Chemistry II, University of the Basque Country (UPV/EHU), P.O. Box 644, 48080 Bilbao, Spain. marisa.carrillo@ehu.es joseluis.vicario@ehu.es.
authors.forename: Uxue
authors.initials: U
authors.lastname: Uria
authors.affiliation: Department of Organic Chemistry II, University of the Basque Country (UPV/EHU), P.O. Box 644, 48080 Bilbao, Spain. marisa.carrillo@ehu.es joseluis.vicario@ehu.es.
authors.forename: Efraím
authors.initials: E
authors.lastname: Reyes
authors.affiliation: Department of Organic Chemistry II, University of the Basque Country (UPV/EHU), P.O. Box 644, 48080 Bilbao, Spain. marisa.carrillo@ehu.es joseluis.vicario@ehu.es.
authors.forename: Luisa
authors.initials: L
authors.lastname: Carrillo
authors.affiliation: Department of Organic Chemistry II, University of the Basque Country (UPV/EHU), P.O. Box 644, 48080 Bilbao, Spain. marisa.carrillo@ehu.es joseluis.vicario@ehu.es.
authors.forename: Jose L
authors.initials: JL
authors.lastname: Vicario
mesh_terms: D002929:Cinchona / Q000737:chemistry*; D009930:Organic Chemicals / Q000737:chemistry*; D011392:Proline / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D009930:Organic Chemicals; D011392:Proline