Tricks of the trade: Because intramolecular Cu-catalyzed access to bicyclo[4.2.0]octanes is not feasible, an oxygen bridge was introduced to facilitate the [2+2] photocycloaddition. Starting from compounds similar to 1, products such as 2 could be obtained enantioselectiviely in three steps after ring-opening metathesis (see scheme).
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http://dx.doi.org/10.1002/chem.201302882 | DOI Listing |
Chem Commun (Camb)
May 2024
Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research (NIPER), Mohali 160062, India.
A unified strategy is disclosed that builds on successfully engaging the aniline nitrogen of 1,3-amphoteric γ-aminocyclopentenone for a tandem annulation with electron-poor alkynes, solely assisted by the H-bonding network of HFIP. This metal-free mild strategy provides access to medicinally relevant aza-bicyclo-octanes en route to another important scaffold: cyclopenta[]pyrrole.
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