Synthesis of optically active trifluoromethylated indolizidine derivatives via stereoselective radical cyclization.
[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.
Okano
Takashi
T
Department of Applied Chemistry, Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa-ku, Nagoya 464-8603, Japan. okano@apchem.nagoya-u.ac.jp
Fumoto
Masataka
M
Kusukawa
Takahiro
T
Fujita
Makoto
M
D018360:Crystallography, X-Ray; D003500:Cyclization; D006868:Hydrolysis; D007212:Indolizines / Q000138:chemical synthesis*; D010100:Oxygen / Q000737:chemistry; D013237:Stereoisomerism
D007212:Indolizines; D010100:Oxygen