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Synthesis of bicyclo[3.1.0]hexanes by (3 + 2) annulation of cyclopropenes with aminocyclopropanes.
Journal article

Synthesis of bicyclo[3.1.0]hexanes by (3 + 2) annulation of cyclopropenes with aminocyclopropanes.

  • Muriel B Laboratory of Catalysis and Organic Synthesis , Institut des Sciences et Ingénierie Chimique , Ecole Polytechnique Fédérale de Lausanne , Lausanne , Ch-1015 , Switzerland . Email: jerome.waser@epfl.ch.
  • Gagnebin A Laboratory of Catalysis and Organic Synthesis , Institut des Sciences et Ingénierie Chimique , Ecole Polytechnique Fédérale de Lausanne , Lausanne , Ch-1015 , Switzerland . Email: jerome.waser@epfl.ch.
  • Waser J Laboratory of Catalysis and Organic Synthesis , Institut des Sciences et Ingénierie Chimique , Ecole Polytechnique Fédérale de Lausanne , Lausanne , Ch-1015 , Switzerland . Email: jerome.waser@epfl.ch.
  • 2020-02-29
Published in:
  • Chemical science. - 2019
General Chemistry
English 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.
Language
  • English
Open access status
gold
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Persistent URL
https://sonar.ch/global/documents/190596
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