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Asymmetric alkylation catalyzed by chiral alkali metal alkoxides of TADDOL. Synthesis of α-methyl amino acids

  • Organic Chemistry
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

It is shown that sodium alkoxides formed from (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-bis(diphenylmethanol) ((R,R)-TADDOL) and some of its derivatives can be used as chiral catalysts for enantioselective alkylation of Schiff's bases derived from alanine with reactive alkyl halides. Acid hydrolysis of the reaction products affords (R)-α-methylphenyl-alanine, (R)-α-allylalanine, and (R)-α-methylnaphthylalanine in 61–93% yields and withee 69–94%. When (S,S)-TADDOL is used, the (S)-amino acid is formed. A mechanism explaning the observed features of the reaction is proposed.

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Authors and Affiliations

  1. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 117813, Moscow, Russian Federation

    Yu. N. Belokon, K. A. Kochetkov, T. D. Churkina & N. S. Ikonnikov

  2. Higher Chemical College, Russian Academy of Sciences, 9 Miusskaya pl., 125820, Moscow, Russian Federation

    A. A. Chesnokov & O. V. Larionov

  3. Institut de Chimie Moleculaire d'Orsay, Universite de Paris Sud. 91405, URA CNRS 1497, Orsay Cedex, France

    H. V. Kagan

Authors
  1. Yu. N. Belokon
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  2. K. A. Kochetkov
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  3. T. D. Churkina
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  4. N. S. Ikonnikov
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  5. A. A. Chesnokov
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  6. O. V. Larionov
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  7. H. V. Kagan
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Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 926–932, May, 1999.

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Belokon, Y.N., Kochetkov, K.A., Churkina, T.D. et al. Asymmetric alkylation catalyzed by chiral alkali metal alkoxides of TADDOL. Synthesis of α-methyl amino acids. Russ Chem Bull 48, 917–923 (1999). https://doi.org/10.1007/BF02494637

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  • DOI: https://doi.org/10.1007/BF02494637

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