title: Enantioselective synthesis of pyrrolidine-, piperidine-, and azepane-type N-heterocycles with α-alkenyl substitution: the CpRu-catalyzed dehydrative intramolecular N-allylation approach.
abstract: A cationic CpRu complex of chiral picolinic acid derivatives [(R)- or (S)-Cl-Naph-PyCOOCH(2)CH═CH(2)] catalyzes asymmetric intramolecular dehydrative N-allylation of N-substituted ω-amino- and -aminocarbonyl allylic alcohols with a substrate/catalyst ratio of up to 2000 to give α-alkenyl pyrrolidine-, piperidine-, and azepane-type N-heterocycles with an enantiomer ratio of up to >99:1. The wide range of applicable N-substitutions, including Boc, Cbz, Ac, Bz, acryloyl, crotonoyl, formyl, and Ts, significantly facilitates further manipulation toward natural product synthesis.
authors.affiliation: Research Center for Materials Science and the Department of Chemistry, Nagoya University, Chikusa, Nagoya 464-8602, Japan.
authors.forename: Tomoaki
authors.initials: T
authors.lastname: Seki
authors.forename: Shinji
authors.initials: S
authors.lastname: Tanaka
authors.forename: Masato
authors.initials: M
authors.lastname: Kitamura
mesh_terms: D001381:Azepines / Q000138:chemical synthesis*; D002384:Catalysis; D015394:Molecular Structure; D010880:Piperidines / Q000138:chemical synthesis*; D011759:Pyrrolidines / Q000138:chemical synthesis*; D017975:Ruthenium Compounds / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D001381:Azepines; D010880:Piperidines; D011759:Pyrrolidines; D017975:Ruthenium Compounds; C032727:piperidine; C032519:pyrrolidine