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Synthesis of enantiomeric (+)- and (-)-6-(1-methylethylidene)-3,3a,6,6a-tetrahydro-2H-cyclopenta[b]furan-1-ones

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Abstract

Baeyer-Villiger oxidation of racemic [2 +2 ]-cycloadduct derived from dichloroketene and dimethylfulvene gave 3,3-dichloro-6-(1-methylidene)-3,3a,6,6a-tetrahydro-2H-cyclopenta[b]furan-2-one, and opening of the lactone ring in the latter with (+)-α-methylbenzylamine produced diastereoisomeric amides which can be readily separated by chromatography on silica gel. The subsequent lactonization and reductive dechlorination afforded enantiomeric (−)- and (+)-6-(propan-2-ylidene)-3,3a,6,6a-tetrahydro-2H-cyclopenta[b]-furan-1-ones.

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Authors and Affiliations

  1. Institute of Organic Chemistry, Ufa Research Center, Russian Academy of Sciences, pr. Oktyabrya 71, Ufa, 450054, Bashkortostan, Russia

    N. A. Ivanova, V. A. Akhmetyanova, N. P. Akhmetdinova, O. V. Shitikova & M. S. Miftakhov

  2. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, ul. Vavilova 28, Moscow, 119991, Russia

    K. Yu. Suponitzky

Authors
  1. N. A. Ivanova
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  2. V. A. Akhmetyanova
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  3. N. P. Akhmetdinova
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  4. O. V. Shitikova
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  5. K. Yu. Suponitzky
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  6. M. S. Miftakhov
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Correspondence to N. A. Ivanova.

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Original Russian Text © N.A. Ivanova, V.A. Akhmetyanova, N.P. Akhmetdinova, O.V. Shitikova, K.Yu. Suponitzky, M.S. Miftakhov, 2014, published in Zhurnal Organicheskoi Khimii, 2014, Vol. 50, No. 6, pp. 828–832.

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Ivanova, N.A., Akhmetyanova, V.A., Akhmetdinova, N.P. et al. Synthesis of enantiomeric (+)- and (-)-6-(1-methylethylidene)-3,3a,6,6a-tetrahydro-2H-cyclopenta[b]furan-1-ones. Russ J Org Chem 50, 810–814 (2014). https://doi.org/10.1134/S1070428014060098

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  • DOI: https://doi.org/10.1134/S1070428014060098

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