Abstract
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.
Supplementary materials
Title
Synthesis
Description
Detailed synthetic procedures, characterization of new product, and copies of NMR spectra
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Title
Calculations
Description
DFT calculation of redox potentials and acidity constants
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Title
Electrochemistry
Description
Electrochemical studies of cyclic and bicyclic amines
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