Journal
CHEMICAL SCIENCE
Volume 10, Issue 46, Pages 10716-10722Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c9sc03790j
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Funding
- Swiss National Science Foundation [200021_165788]
- EPFL
- Swiss National Science Foundation (SNF) [200021_165788] Funding Source: Swiss National Science Foundation (SNF)
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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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