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Stereochemistry of the reduction of the carbonyl function of 3-ketopiperidines: Influence of a bulky e-substituent at C4

  • Organic Chemistry
  • Published:
Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Conclusions

We synthesized 1,4-di-tert-butyl- and 1-tert-butyl-4-isopropylpiperid-3-ones and studied the stereochemistry of their reduction. With the increase in the size of the substituent at C2, there is increasing obstruction to the attack of the reagent at the carbonyl from the axial region.

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Literature cited

  1. G. T. Katvalyan, N. A. Semenova, and É. A. Mistryukov, Izv. Akad. Nauk SSSR., Ser. Khim., 1806 (1976).

  2. G. T. Katvalyan, N. A. Semenova, and É. A. Mistryukov, Izv. Akad. Nauk SSSR, Ser. Khim., 129 (1976).

  3. E. A. Mistryukov and G. T. Katvalyan, Izv. Akad. Nauk SSSR, Ser. Khim., 702 (1969).

  4. J. Ficini and A. Manjean, Bull. Soc. Chim. France, 219 (1971).

  5. G. T. Katvalyan and E. A. Mistryukov, Izv. Akad. Nauk SSSR, Ser. Khim., 576 (1979).

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Authors and Affiliations

  1. N. D. Zelinskii Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow

    G. T. Katvalyan & É. A. Mistryukov

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  1. G. T. Katvalyan
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  2. É. A. Mistryukov
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 10, pp. 2328–2331, October, 1985.

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Katvalyan, G.T., Mistryukov, É.A. Stereochemistry of the reduction of the carbonyl function of 3-ketopiperidines: Influence of a bulky e-substituent at C4 . Russ Chem Bull 34, 2156–2159 (1985). https://doi.org/10.1007/BF00963253

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  • DOI: https://doi.org/10.1007/BF00963253

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