title: An aza-Prins cyclization approach to functionalized indolizidines from 2-allylpyrrolidines.
abstract: The stereoselective synthesis of a diverse set of functionalized indolizidine systems has been accomplished through the aza-Prins cyclization of 2-allylpyrrolidines. The condensation of aldehydes onto 2-allylpyrrolidines yields iminium ions that undergo highly diastereoselective aza-Prins cyclization, producing up to two stereogenic centers and two new rings in one step.
authors.affiliation: Department of Chemistry, The University of Vermont, 82 University Place, Burlington, Vermont 05405, USA.
authors.forename: Xiaoxi
authors.initials: X
authors.lastname: Liu
authors.forename: Michael P
authors.initials: MP
authors.lastname: McCormack
authors.forename: Stephen P
authors.initials: SP
authors.lastname: Waters
mesh_terms: D002384:Catalysis; D003500:Cyclization; D054836:Indolizidines / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D011759:Pyrrolidines / Q000737:chemistry*
chemical_list: D054836:Indolizidines; D011759:Pyrrolidines