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Synthesis of nonracemic polysubstituted cyclohexanes through cascade reactions of (2R,3S)-2-Acetyl-3-aryl-4-nitrobutanoates, adducts of Ni(II)-catalyzed michael addition

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Abstract

Stereoselective synthesis of ethyl-4,6-diaryl-2-hydroxy-2-methyl-5-nitro-3-formylcyclohexanecarboxylates was described. The formation of the asymmetric site of the required configuration is achieved by an enantioselective Michael addition of ethyl acetoacetate to nitroalkenes in the presence of a chiral Ni(II) complex with (R,R)-N,N′-dibenzylcyclohexane-1,2-diamine. Further reaction of the products obtained with cinnamic aldehyde led to the formation of polysubstituted cyclohexanes.

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Authors and Affiliations

  1. Samara State Technical University, Samara, Russia

    A. N. Reznikov, E. A. Sidnin & Yu. N. Klimochkin

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  1. A. N. Reznikov
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  2. E. A. Sidnin
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  3. Yu. N. Klimochkin
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Correspondence to A. N. Reznikov.

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Original English Text © A.N. Reznikov, E.A. Sidnin, Yu.N. Klimochkin, 2013, published in Zhurnal Organicheskoi Khimii, 2013, Vol. 49, No. 11, pp. 1623–1626.

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Reznikov, A.N., Sidnin, E.A. & Klimochkin, Y.N. Synthesis of nonracemic polysubstituted cyclohexanes through cascade reactions of (2R,3S)-2-Acetyl-3-aryl-4-nitrobutanoates, adducts of Ni(II)-catalyzed michael addition. Russ J Org Chem 49, 1600–1604 (2013). https://doi.org/10.1134/S1070428013110067

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  • DOI: https://doi.org/10.1134/S1070428013110067

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