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Communication | Special issue | Vol 76, No. 1, 2008, pp.177-182
Published online, 17th April, 2008
DOI: 10.3987/COM-08-S(N)26
Regioselective Introduction of Electrophiles into Piperidine Derivatives at the 4-Position

Osamu Onomura,* Noriyuki Fujimura, Takahisa Oda, Yoshihiro Matsumura, and Yosuke Demizu

*Department of Pharmaceutical Sciences, Graduate School of Biomedical Sciences, Nagasaki University, 1-14 Bunkyo-machi, Nagasaki 852-8521, Japan

Abstract

Regioselective introduction of various electrophiles (aldehydes, ketones, and imines) into piperidine skeleton at the 4-position was achieved with a catalytic amount of Pd(OAc)2/PPh3 in the presence of excess Et2Zn. In addition, enantioselective introduction of benzaldehyde into piperidine derivatives was accomplished by using chiral phosphine ligand with moderate enantioselectivity.