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Donor-acceptor bicyclopropyl configuration-fixed by an additional trimethylene bridge: synthesis and Lewis acid-catalyzed tandem three-membered rings opening

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Abstract

A diastereoselective synthesis of donor-acceptor bicyclopropyl, 8-phenyldispiro[2.3.2.0]-nonane-1,1-dicarboxylate, was carried out, which treated with Lewis acids acts as a synthetic equivalent of cis-1,6-zwitterionic intermediates. In the presence of GaCl3, the main direction is 1,6-cyclization to the substituted 1,2,3,4,6,7-hexahydro-5H-indene, while the action of EtAlCl2 triggers the three-membered rings opening, leading to the ethylation at the carbocation center. The reaction of 8-phenyldispiro[2.3.2.0]nonane-1,1-dicarboxylate with 4-phenyl-1,2,4-triazoline-3,5-dione in the presence of 10 mol.% of Yb(OTf)3 proceeds through the ionic [6+2] cycloaddition of 1,6-zwitterion to the N=N bond with the formation of an eight-membered heterocycle.

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Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    D. A. Denisov, R. A. Novikov & Yu. V. Tomilov

Authors
  1. D. A. Denisov
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  2. R. A. Novikov
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  3. Yu. V. Tomilov
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Corresponding authors

Correspondence to R. A. Novikov or Yu. V. Tomilov.

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This paper does not contain descriptions of studies on animals or humans.

The authors declare no competing interests.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1568–1574, August, 2021.

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Denisov, D.A., Novikov, R.A. & Tomilov, Y.V. Donor-acceptor bicyclopropyl configuration-fixed by an additional trimethylene bridge: synthesis and Lewis acid-catalyzed tandem three-membered rings opening. Russ Chem Bull 70, 1568–1574 (2021). https://doi.org/10.1007/s11172-021-3253-9

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  • DOI: https://doi.org/10.1007/s11172-021-3253-9

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