Synthesis of chiral phosphorus reagents and their catalytic activity in asymmetric borane reduction of N-phenyl imine of acetophenone

Eleven chiral trivalent or quatrivalent phosphorus reagents were synthesized starting from <SC>L</SC>-proline, <SC>D</SC>-camphor, (+)- or (−)-1,1'-binaphthalene-2,2'-diol, (−)-α-phenylethylamine, etc. and their application as catalysts in asymmetric borane reduction of N-phenyl imine of acetophenone was preliminarily investigated. N-Phenyl α-phenylethylamine was obtained in good yield with low to moderate enantioselectivity. © 2003 Wiley Periodicals, Inc. Heteroatom Chem 14:546–550, 2003; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.10190