Pure Appl. Chem., 2008, Vol. 80, No. 5, pp. 1109-1113
doi: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
1Catalysis Research Center and Graduate School of Life Science, Hokkaido University, and SORST, Japan Science and Technology Agency (JST), Kita-ku, Sapporo 001-0021, Japan; 2Department 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.
Keywords: asymmetric synthesis; diastereoselective; enantioselective; ferrocene; kinetic resolution; metathesis; molybdenum; planar-chiral; ruthenium.
*Paper based on a presentation at the 14th International Symposium on Organometallic Chemistry Directed Towards Organic Synthesis (OMCOS-14), 2-6 August 2007, Nara, Japan. Other presentations are published in this issue, pp. 807-1194.
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