title: Nucleophilic phosphine-catalyzed intramolecular Michael reactions of N-allylic substituted α-amino nitriles: construction of functionalized pyrrolidine rings via 5-endo-trig cyclizations.
abstract: Pyrrolidine rings are common moieties for pharmaceutical candidates and natural compounds, and the construction of these skeletons has received much attention. α-Amino nitriles are versatile intermediates in synthetic chemistry and have been widely used in the generation of multiple polyfunctional structures. Herein, a novel nucleophilic phosphine-catalyzed intramolecular Michael reaction of N-allylic substituted α-amino nitriles has been developed for the efficient construction of functionalized 2,4-disubstituted pyrrolidines (N-heterocyclic α-amino nitriles) via 5-endo-trig cyclization. Furthermore, the one-pot sequence of the synthesis of pyrrolidine and the subsequent transformations of the functionalized products have also been demonstrated.
authors.affiliation: Department of Organic Chemistry, College of Chemistry, Jilin University , 2699 Qianjin Street, Changchun 130012, China.
authors.forename: Da
authors.initials: D
authors.lastname: En
authors.forename: Gong-Feng
authors.initials: GF
authors.lastname: Zou
authors.forename: Yuan
authors.initials: Y
authors.lastname: Guo
authors.forename: Wei-Wei
authors.initials: WW
authors.lastname: Liao
mesh_terms: D002384:Catalysis; D003500:Cyclization; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D010720:Phosphines / Q000737:chemistry*; D011759:Pyrrolidines / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D006571:Heterocyclic Compounds; D009570:Nitriles; D010720:Phosphines; D011759:Pyrrolidines; C044646:phosphine; C032519:pyrrolidine