Gesellschaft Deutscher Chemiker
Keine Benachrichtigungen
Sie haben noch keine Lesezeichen


Synergistic Catalysis between a Dipeptide Phosphonium Salt and a Metal‐Based Lewis Acid for Asymmetric Synthesis of N‐Bridged [3.2.1] Ring Systems

Von Wiley-VCH zur Verfügung gestellt

A synergic catalytic method for asymmetric construction of N-bridged [3.2.1] rings by a phosphonium salt/silver co-catalyzed cyclization has been developed. This route affords fluorine-installed tropane derivatives in excellent stereoselectivities. The mechanistic results revealed that the silver nitrite was installed on the phosphonium salt via hydrogen bonding and simultaneously activated the dipole, in a “sandwich” reaction model.


We present an unprecedented synergic catalytic route for the asymmetric construction of fluorinated N-bridged [3.2.1] cyclic members of tropane family via a bifunctional phosphonium salt/silver co-catalyzed cyclization process. A broad variety of substrates bearing an assortment of functional groups are compatible with this method, providing targeted compounds bearing seven-membered ring and four contiguous stereocenters in high yields with excellent stereoselectivities. The gram-scale preparations, facile elaborations and preliminary biological activities of the products demonstrate the application potential. Moreover, both experimental and computational mechanistic studies revealed that the cyclization proceeded via a “sandwich” reaction model with multiple weak-bond cooperative activations. Insights gained from our studies are expected to advance general efforts towards the catalytic synthesis of challenging chiral heterocyclic molecules.

Zum Volltext

Überprüfung Ihres Anmeldestatus ...

Wenn Sie ein registrierter Benutzer sind, zeigen wir in Kürze den vollständigen Artikel.