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Paper | Special issue | Vol 82, No. 1, 2010, pp.325-332
Published online, 22nd February, 2010
DOI: 10.3987/COM-09-S(E)2
Mannich-Type Reaction of N,O-Acetals with Ketones Mediated by a Combination of TiCl4 and PhSiCl3

Satoshi Kamogawa, Takashi Ikeda, Masami Kuriyama, Yoshihiro Matsumura, and Osamu Onomura*

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

Abstract

A combination of TiCl4 and PhSiCl3 efficiently conducts the Mannich-type reaction of N,O-acetals with ketones to afford α-substituted cyclic amine derivatives in good yields. This method was applicable to preparation of azabicyclo compounds by the intramolecular Mannich-type reaction.