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Stereochemistry of the asymmetric reduction of N-(α-phenylethyl)-δ8,9-hexahydro-4-pyrindone

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Abstract

The reduction of optically active N-(α-phenylethyl)-Δ8,9-hexahydro-4-pyrindone with lithium aluminum hydride proceeds as asymmetric stereospecific 1,4-hydride addition an leads to the formation of primarily the thermodynamically stable trans-(8S,9S)-N-(α-phenylethyl) octahydro-4-pyrindone and a small amount of the corresponding cis isomer. Only cis-(8S,9S)-octahydro-4-pyrindone was obtained from each isomer and the mixture of isomers after removal of the chiral substituent from the nitrogen atom. The absolute configurations of the compounds obtained were established on the basis of circular dichroism data and the octant rule.

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Literature cited

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Authors and Affiliations

  1. M. V. Lomonosov Moscow State University, 117234, Moscow

    G. V. Grishina, V. M. Potapov & T. A. Liberchuk

Authors
  1. G. V. Grishina
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  2. V. M. Potapov
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  3. T. A. Liberchuk
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Additional information

Communication XLVIII from “Stereochemical Studies.” See [1] for communication XLVII.

Translated from Khimiya Getero-tsiklicheskikh Soedinenii, No. 2, pp. 240–245, February, 1978.

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Grishina, G.V., Potapov, V.M. & Liberchuk, T.A. Stereochemistry of the asymmetric reduction of N-(α-phenylethyl)-δ8,9-hexahydro-4-pyrindone. Chem Heterocycl Compd 14, 194–199 (1978). https://doi.org/10.1007/BF00945334

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  • DOI: https://doi.org/10.1007/BF00945334

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