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Asymmetric synthesis, stereochemistry, and absolute configuration of 1,2-5-trimethyl-5-(2-cyanoethyl)- and 1,2,5-trimethyl-4-piperidinones

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Abstract

The asymmetric Michael alkylation of (−)-1,2,5-trimethyl-4-(1S-phenylethylimino)piperidine by electrondeficient alkenes proceeds with the formation of(+)-cis-(2S,5S)- and (−)-trans-(2R,5S) diastereomers of 1,2,5-trimethyl-5-(2-cyanoethyl)- and 1,2,5-trimethyl-5-(2-methoxycarbonylethyl)-4-piperidinones containing a chiral quaternary center C(5). The spatial structure of these new chiral 4-piperidinones has been established on the basis of 1H and 13C NMR spectroscopic data. The absolute configuration of the C(2) and c(5) chiral centers in the diastereomers has been determined by stereochemical correlation on the basis of circular dichroism data.

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Authors and Affiliations

  1. M. V. Lomonosov Moscow State University, 119899, Moscow

    G. V. Grishina, E. L. Gaidarova & A. É. Aliev

Authors
  1. G. V. Grishina
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  2. E. L. Gaidarova
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  3. A. É. Aliev
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1369–1378, October, 1992.

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Grishina, G.V., Gaidarova, E.L. & Aliev, A.É. Asymmetric synthesis, stereochemistry, and absolute configuration of 1,2-5-trimethyl-5-(2-cyanoethyl)- and 1,2,5-trimethyl-4-piperidinones. Chem Heterocycl Compd 28, 1166–1174 (1992). https://doi.org/10.1007/BF00529581

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  • DOI: https://doi.org/10.1007/BF00529581

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