title: Asymmetric synthesis of 2,5-disubstituted 3-hydroxypyrrolidines based on stereodivergent intramolecular iridium-catalyzed allylic aminations.
abstract: Intramolecular iridium-catalyzed allylic aminations of homochiral (E)-6-N-nosylaminohept-2-en-1-yl methyl carbonates were investigated. The relative position of the 2,5-substituents of the resulting pyrrolidines was found to be controlled by using both enantiomers (4 and 5) of the appropriate chiral ligand, demonstrating a simple and highly stereodivergent synthetic protocol. Selected trans- and cis-2,5-disubstituted 3-hydroxypyrrolidines (2a and 18a) were converted to (+)-bulgecinine (6) and (+)-preussin (7), respectively.
authors.affiliation: Faculty of Pharmaceutical Sciences, Tohoku Pharmaceutical University, Sendai 981-8558, Japan.
authors.forename: Yoshihiro
authors.initials: Y
authors.lastname: Natori
authors.forename: Shunsuke
authors.initials: S
authors.lastname: Kikuchi
authors.forename: Takahiro
authors.initials: T
authors.lastname: Kondo
authors.forename: Yukako
authors.initials: Y
authors.lastname: Saito
authors.forename: Yuichi
authors.initials: Y
authors.lastname: Yoshimura
authors.forename: Hiroki
authors.initials: H
authors.lastname: Takahata
mesh_terms: D000498:Allyl Compounds / Q000737:chemistry*; D000586:Amination; D002384:Catalysis; D007495:Iridium / Q000737:chemistry*; D008968:Molecular Conformation; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000498:Allyl Compounds; D011759:Pyrrolidines; D007495:Iridium