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Synthesis of Bicyclo[3.1.0]hexanes by (3+2) Annulation of Cyclopropenes with Aminocyclopropanes

Abstract

We report the convergent synthesis of bicyclo[3.1.0]hexanes possessing an all-carbon quaternary center via a (3+2) annulation of cyclopropenes with cyclopropylanilines. Using an organic or an iridium photoredox catalyst and blue LED irradiation, good yields were obtained for a broad range of cyclopropene and cyclopropylaniline derivatives. The reaction was highly diastereoselective when using difluorocyclopropenes together with a removable substituent on the cyclopropylaniline, giving access to important building blocks for medicinal chemistry. With efficient methods existing for the synthesis of both reaction partners, our method grants a fast access to highly valuable bicyclic scaffolds with three contiguous stereocenters.

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Publication details

The article was received on 31 Jul 2019, accepted on 07 Oct 2019 and first published on 08 Oct 2019


Article type: Edge Article
DOI: 10.1039/C9SC03790J
Chem. Sci., 2019, Accepted Manuscript
  • Open access: Creative Commons BY-NC license
    All publication charges for this article have been paid for by the Royal Society of Chemistry

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    Synthesis of Bicyclo[3.1.0]hexanes by (3+2) Annulation of Cyclopropenes with Aminocyclopropanes

    B. Muriel, A. Gagnebin and J. Waser, Chem. Sci., 2019, Accepted Manuscript , DOI: 10.1039/C9SC03790J

    This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. Material from this article can be used in other publications provided that the correct acknowledgement is given with the reproduced material and it is not used for commercial purposes.

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