Asymmetric synthesis of planar-chiral ferrocenes by Mo- or Ru-catalyzed enantioselective metathesis

Ogasawara, Masamichi; Watanabe, Susumu; Nakajima, Kiyohiko; Takahashi, Tamotsu

doi:10.1351/pac200880051109

Pure Appl. Chem., 2008, Vol. 80, No. 5, pp. 1109-1113

http://dx.doi.org/10.1351/pac200880051109

Asymmetric synthesis of planar-chiral ferrocenes by Mo- or Ru-catalyzed enantioselective metathesis

Masamichi Ogasawara¹, Susumu Watanabe¹, Kiyohiko Nakajima² and Tamotsu Takahashi¹

¹ Catalysis Research Center and Graduate School of Life Science, Hokkaido University, and SORST, Japan Science and Technology Agency (JST), Kita-ku, Sapporo 001-0021, Japan
² Department of Chemistry, Aichi University of Education, Igaya, Kariya 448-8542, Japan

Abstract: Kinetic resolution of planar-chiral 1,1'-diallylferrocene derivatives was realized by Mo- or Ru-catalyzed asymmetric ring-closing metathesis (RCM). The Mo catalyst showed much better performance than the Ru catalyst in the present reactions, and nearly perfect resolution of the racemic ferrocenes was achieved. This is the first example of highly enantioselective metal-catalyzed methods of preparing optically active planar-chiral metallocenes.