title: Organocatalytic Activation of the Leaving Group in the Intramolecular Asymmetric SN 2' Reaction.
abstract: A Brønsted-acid-catalyzed intramolecular enantioselective SN 2' reaction was developed utilizing trichloroacetimidate as a leaving group. The findings indicated that dual activation of the substrates is operative. This metal-free allylic alkylation allows highly enantioselective access to 2-vinylpyrrolidines bearing various substituents.
authors.affiliation: Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501 (Japan).
authors.forename: Yusuke
authors.initials: Y
authors.lastname: Kuroda
authors.affiliation: Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501 (Japan).
authors.forename: Shingo
authors.initials: S
authors.lastname: Harada
authors.affiliation: Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501 (Japan).
authors.forename: Akinori
authors.initials: A
authors.lastname: Oonishi
authors.affiliation: Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501 (Japan).
authors.forename: Yousuke
authors.initials: Y
authors.lastname: Yamaoka
authors.affiliation: Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501 (Japan). yamak@pharm.kyoto-u.ac.jp.
authors.forename: Ken-Ichi
authors.initials: K
authors.lastname: Yamada
authors.affiliation: Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501 (Japan). kay-t@pharm.kyoto-u.ac.jp.
authors.forename: Kiyosei
authors.initials: K
authors.lastname: Takasu
mesh_terms: D000498:Allyl Compounds / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D011759:Pyrrolidines / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000498:Allyl Compounds; D011759:Pyrrolidines
keywords: asymmetric catalysis; nucleophilic substitution; organocatalysis; pyrrolidines