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Synlett 1995; 1995(1): 79-81
DOI: 10.1055/s-1995-4881
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Asymmetric Synthesis and Highly Diastereoselective ortho-Lithiation of Oxazolinylferrocenes

Yoshiaki Nishibayashi, Sakae Uemura*
  • *Division of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University, Sakyo-ku, Kyoto 606-01, Japan
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Publication Date:
31 December 2000 (online)

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Highly diastereoselective ortho-lithiation (84-99% de) of chiral oxazolinylferrocenes followed by quenching with an electrophile such as MeI, PPh2Cl or (PhSe)2 leading to the corresponding ortho-substituted ferrocenes is accomplished. The molecular structure of a phenylseleno-substituted compound, fully characterized by X-ray crystallography, showed the attack of the electrophile from the unexpected site.

diastereoselective lithiation - oxazolinylferrocenes - hydrosilylation - rhodium