title: Synthesis of optically active trifluoromethylated indolizidine derivatives via stereoselective radical cyclization.
abstract: [reaction: see text]. Asymmetric Michael reaction of lithiated trifluoroacetone SAMP-hydrazone with alkylidenemalonates gave addition products stereoselectively. Hydrolyzed enantiomerically pure ketoacids were cyclized to dihydropyridinones. N-Iodopropylation followed by radical cyclization gave optically active trifluoromethylated indolizidinones stereoselectively.
authors.affiliation: Department of Applied Chemistry, Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa-ku, Nagoya 464-8603, Japan. okano@apchem.nagoya-u.ac.jp
authors.forename: Takashi
authors.initials: T
authors.lastname: Okano
authors.forename: Masataka
authors.initials: M
authors.lastname: Fumoto
authors.forename: Takahiro
authors.initials: T
authors.lastname: Kusukawa
authors.forename: Makoto
authors.initials: M
authors.lastname: Fujita
mesh_terms: D018360:Crystallography, X-Ray; D003500:Cyclization; D006868:Hydrolysis; D007212:Indolizines / Q000138:chemical synthesis*; D010100:Oxygen / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D007212:Indolizines; D010100:Oxygen