Tropane and Related Alkaloid Skeletons via a Radical [3+3]-Annulation Process Article Swipe

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Annulation Chemistry Radical cyclization Bicyclic molecule Deprotonation Octane Tropane Reactivity (psychology) Radical Photoredox catalysis Stereochemistry Organic chemistry Catalysis Photocatalysis Medicine Ion Alternative medicine Pathology

Eloïse Colson , Julie Andrez , Ali Dabbous , F. Dénès , Vincent Maurel , Jean‐Marie Mouesca , Philippe Renaud ·

YOU? · · 2021 · Open Access · · DOI: https://doi.org/10.26434/chemrxiv-2021-gq1jb · OA: W4225524321

A mild and simple protocol for the synthesis of 8-azabicyclo[3.2.1]octane and 9-azabicyclo[3.3.1]nonane derivatives is described. It provides these valuable bicyclic alkaloid skeletons in good yields and high levels of diastereoselectivity from simple and readily available starting materials using visible-light photoredox catalysis. This unprecedented annulation process takes advantage of the unique reactivity of ethyl 2-(acetoxymethyl)acrylate as a 1,3-bis radical acceptor and of cyclic N,N-dialkylanilines as radical 1,3-bis radical donors. The success of this process relies on efficient electron transfer processes and highly selective deprotonation of aminium radical cations leading to the key α-amino radical intermediates.