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Synlett 2001; 2001(8): 1275-1277
DOI: 10.1055/s-2001-16066
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Diastereoselective Addition of Organometallics to Chiral Amino Formyl- and Acylferrocenes: Synthesis of A Chiral 1,2-Homo Disubstituted Ferrocene

Shin-ichi Fukuzawa* , Kuniaki Fujimoto
  • *Department of Applied Chemistry, Institute of Science and Engineering, Chuo University, Kasuga, Bunkyo-ku, Tokyo 112-8551, Japan; Fax 81-(0)3-38 17-18 95; E-mail: fukuzawa@chem.chuo-u.ac.jp
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Publication Date:
31 December 2001 (online)

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The addition of Grignard reagents to the ortho-aminoformylferrocene (4) gave the corresponding amino alcohol (5 a) of which the chiral center of the newly formed alcoholic carbon had the R configuration as the major diastereomer in 26-82% de. On the other hand, the stereochemical outcome was in contrast to the dialkylzinc addition to 7, the alcoholic carbon being the S configuration. The reduction of the chiral ortho-aminobenzoylferrocenes (7, 8) with DIBAH gave the corresponding amino alcohol (5 a, 9 a) with the R configuration of the alcoholic carbon as single diastereomers, while the reduction with LiAlH4 produced them with the S configuration of the alcoholic carbon as major diastereomers.

metallocenes - asymmetric synthesis - nucleophilic additions - chiral auxiliaries - iron - stereoselectivity