Rhodium-catalyzed asymmetric 1,4-addition of organoboron reagents to 5,6-dihydro-2(1H)-pyridinones. Asymmetric synthesis of 4-aryl-2-piperidinones.
Catalytic asymmetric synthesis of 4-aryl-2-piperidinones was realized for the first time by asymmetric 1,4-addition of arylboron reagents to 5,6-dihydro-2(1H)-pyridinones in the presence of a chiral bisphosphine-rhodium catalyst. In the reaction introducing 4-fluorophenyl group, the use of 4-fluorophenylboroxine and 1 equiv (to boron) of water at 40 degrees C gave the highest yield of the arylation product with high enantioselectivity (98% ee). The (R)-4-(4-fluorophenyl)-2-piperidinone obtained here is a key intermediate for the synthesis of (-)-Paroxetine.
Senda
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Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502, Japan.
Ogasawara
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Hayashi
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D001896:Boron Compounds / Q000737:chemistry; D002384:Catalysis; D010881:Piperidones / Q000138:chemical synthesis*; D011728:Pyridones / Q000737:chemistry; D012238:Rhodium / Q000737:chemistry
D001896:Boron Compounds; D010881:Piperidones; D011728:Pyridones; C017679:2-hydroxypyridine; D012238:Rhodium; C043384:2-piperidone