Preparation of arylzinc reagents and their use in the rhodium-catalyzed asymmetric 1,4-addition for the synthesis of 2-aryl-4-piperidones.
A protocol for the catalytic asymmetric synthesis of 2-aryl-4-piperidones with high enantiomeric excess (ee) (typically > or = 99% ee) has been described here. The preparation of arylzinc reagents, which are used as nucleophiles in catalysis, is also included. The whole protocol can be completed in 10-20 h, starting from the preparation of the arylzinc reagents, depending on the reaction time of the rhodium-catalyzed process. A detailed protocol is described using the preparation of 4-fluorophenylzinc chloride and its addition to benzyl 3,4-dihydro-4-oxo-1(2H)-pyridinecarboxylate in the presence of [RhCl((R)-binap)]2 as an example.
Shintani
Ryo
R
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502, Japan. shintani@kuchem.kyoto-u.ac.jp
Hayashi
Tamio
T
D002851:Chromatography, High Pressure Liquid; D007202:Indicators and Reagents; D009942:Organometallic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D010881:Piperidones / Q000138:chemical synthesis*; D011728:Pyridones / Q000737:chemistry; D012238:Rhodium / Q000737:chemistry*; D015032:Zinc / Q000737:chemistry
C526600:4-fluorophenylzinc chloride; D007202:Indicators and Reagents; D009942:Organometallic Compounds; D010881:Piperidones; D011728:Pyridones; C526601:benzyl 3,4-dihydro-4-oxo-1(2H)-pyridinecarboxylate; D012238:Rhodium; D015032:Zinc