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René O, Stepek IA, Gobbi A, et al. Palladium-Catalyzed Ring Expansion of Spirocyclopropanes to Form Caprolactams and Azepanes. J Org Chem. 2015;80(20):10218-25doi: 10.1021/acs.joc.5b01846.
René, O., Stepek, I. A., Gobbi, A., Fauber, B. P., & Gaines, S. (2015). Palladium-Catalyzed Ring Expansion of Spirocyclopropanes to Form Caprolactams and Azepanes. The Journal of organic chemistry, 80(20), 10218-25. https://doi.org/10.1021/acs.joc.5b01846
René, Olivier, et al. "Palladium-Catalyzed Ring Expansion of Spirocyclopropanes to Form Caprolactams and Azepanes." The Journal of organic chemistry vol. 80,20 (2015): 10218-25. doi: https://doi.org/10.1021/acs.joc.5b01846
René O, Stepek IA, Gobbi A, Fauber BP, Gaines S. Palladium-Catalyzed Ring Expansion of Spirocyclopropanes to Form Caprolactams and Azepanes. J Org Chem. 2015 Oct 16;80(20):10218-25. doi: 10.1021/acs.joc.5b01846. Epub 2015 Oct 01. PMID: 26378765.
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J Org Chem. 2015 Oct 16;80(20):10218-25. doi: 10.1021/acs.joc.5b01846. Epub 2015 Oct 01.

Palladium-Catalyzed Ring Expansion of Spirocyclopropanes to Form Caprolactams and Azepanes.

The Journal of organic chemistry

Olivier René, Iain A Stepek, Alberto Gobbi, Benjamin P Fauber, Simon Gaines

Affiliations

  1. Genentech, Incorporated , Discovery Chemistry, 1 DNA Way, South San Francisco, California 94080, United States.
  2. Argenta , Discovery Services, Charles River, 7-9 Spire Green Centre, Flex Meadow, Harlow, Essex CM19 5TR, United Kingdom.

PMID: 26378765 DOI: 10.1021/acs.joc.5b01846

Abstract

A palladium(0)-catalyzed rearrangement of piperidones and piperidines bearing a spirocyclopropane ring was developed. The ring expansion reaction led to a variety of functionalized caprolactam and azepane products in good to excellent yields. Experimental and computational mechanistic studies revealed an initial oxidative addition of the distal carbon-carbon bond of a cyclopropane ring to the palladium(0) catalyst and the relief of ring strain as a driving force for product formation.

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