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Effects of the temperature and substituents in chiral TiIV(salen) catalysts on the enantioselectivity of the addition of Me3SiCN to PhCHO

  • Organic Chemistry
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Abstract

The enantiomeric purity (ee) of the addition product of Me3SiCN to PhCHO at ∼20 °C catalyzed by chiral TiIV complexes, which were preparedin situ from Ti(OPri)4 and the Schiff bases (condensation products of substituted salicylaldehydes with (1R, 2R)-1,2-diaminocyclohexane), was, on the average, 20–30% lower than that achieved at −80 °C. The substituents at position 5 of 3-tert-butylsalicylaldehyde exert only the steric effect. It was shown that the stereochemical result of the reaction is controlled by the stage which involves the formation of the C−C bond rather than the transfer of the Me3Si group.

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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

    V. I. Tararov, N. S. Ikonnikov, V. S. Larichev, M. A. Moscalenko, L. V. Yashkina & Yu. N. Belokon

  2. Department of Chemistry, University of Wales, LL 57'2UW, Bangor, Gwynedd, U.K.

    C. Orizu & M. North

Authors
  1. V. I. Tararov
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  2. C. Orizu
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  3. N. S. Ikonnikov
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  4. V. S. Larichev
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  5. M. A. Moscalenko
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  6. L. V. Yashkina
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  7. M. North
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  8. Yu. N. Belokon
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Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 6, pp. 1139–1141, June, 1999.

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Tararov, V.I., Orizu, C., Ikonnikov, N.S. et al. Effects of the temperature and substituents in chiral TiIV(salen) catalysts on the enantioselectivity of the addition of Me3SiCN to PhCHO. Russ Chem Bull 48, 1128–1130 (1999). https://doi.org/10.1007/BF02496014

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  • DOI: https://doi.org/10.1007/BF02496014

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