Regioselective hydrogenolysis of bis(α-methylbenzyl)amines affected by trifluoromethyl or fluorine substituent on aromatic ring

ORGN 771

Masatomi Kanai1, Manabu Yasumoto1, Yokusu Kuriyama1, Kenjin Inomiya1, Michio Ishida, cgi.ny@sbcglobal.net2, and Akihiro Ishii, aishii@cgco.co.jp1. (1) Chemical Research Center, Central Glass Co., Ltd, 2805, Imafuku-nakadai, Kawagoe Saitama 350-1151, Japan, (2) Chemical Department, Central Glass International, Inc, 50 main street, 8th floor, White Plains, NY 10606
Many new drug candidates for Tachykinin antagonists contain chiral phenethylamine units with fluorine atoms on aromatic rings. Highly regioselective hydrogenolysis of bis(alpha-methylbenzyl)amines proceeded under the influence of trifluoromethyl or fluorine substituent on aromatic ring. In the case of trifluoromethyl substituent, its steric effect played an important role in the regioselective hydrogenolysis.1 On the other hand, electronic effect of fluorine substituent retarded hydrogenolytic cleavage at benzylic position of fluorine-substituted aromatic ring.2 These regioselective hydrogenolyses provided practical asymmetric syntheses of trifluoromethyl- or fluorine-substituted alpha-phenylethylamines. Detail of the reaction mechanism will be discussed.
 

Asymmetric Reactions, Molecular Recognition, Self Assembly, Bioorganic Chemistry, Process R&D
8:00 PM-10:00 PM, Wednesday, 16 March 2005 Convention Center -- Hall D, Poster

Division of Organic Chemistry

The 229th ACS National Meeting, in San Diego, CA, March 13-17, 2005