Stereoselective synthesis of nipecotic acid derivatives via palladium-catalyzed decarboxylative cyclization of gamma-methylidene-delta-valerolactones with imines.
A new synthetic method of multisubstituted nipecotic acid (piperidine-3-carboxylic acid) derivatives has been developed by way of palladium-catalyzed decarboxylative cyclization of gamma-methylidene-delta-valerolactones with imines. By employing the diethoxyphosphinoyl group as the N-protecting group for imines, the reaction proceeds smoothly with high diastereoselectivity. The products thus obtained can be further derivatized with high efficiency under simple reaction conditions.
Shintani
Ryo
R
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502, Japan. shintani@kuchem.kyoto-u.ac.jp
Murakami
Masataka
M
Hayashi
Tamio
T
D002384:Catalysis; D003500:Cyclization; D003653:Decarboxylation; D007097:Imines / Q000737:chemistry*; D009557:Nipecotic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D010165:Palladium / Q000737:chemistry*; D010720:Phosphines / Q000737:chemistry; D011753:Pyrones / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
D007097:Imines; D009557:Nipecotic Acids; D010720:Phosphines; D011753:Pyrones; C052207:delta-valerolactone; C030278:nipecotic acid; D010165:Palladium; C044646:phosphine