1. Synthesis of bicyclo[3.1.0]hexanes by (3 + 2) annulation of cyclopropenes with aminocyclopropanes
- Author
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Bastian Muriel, Jerome Waser, and Alec Gagnebin
- Subjects
pauson-khand reactions ,Annulation ,intramolecular cyclopropanation ,difluorocarbene ,Substituent ,Convergent synthesis ,Cyclopropene ,010402 general chemistry ,01 natural sciences ,Stereocenter ,chemistry.chemical_compound ,nucleoside analogs ,building-blocks ,Bicyclic molecule ,Difluorocarbene ,010405 organic chemistry ,Chemistry ,General Chemistry ,diels-alder reactions ,Combinatorial chemistry ,0104 chemical sciences ,carbonyl ylides ,1,3-dipolar cycloaddition ,rhodium ,1,3-Dipolar cycloaddition ,catalyzed cyclopropanation - 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.
- Published
- 2019
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