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Chemistry

Beng Group Publishes Paper in the Journal of Organic and Biomolecular Chemistry

 Paper title: Expedient and modular access to 2-azabicyclic architectures by iron-catalyzed dehydrative coupling of alcohol-bearing allylic lactams

Citation: Org. Biomol. Chem., 2017, Advance Article, DOI: 10.1039/c6ob02652d

Authors: Katie Hovenkotter, Hannah Braunstein, Spencer Langevin and Timothy K. Beng

 

The pentannulation of readily affordable alcohol-bearing allylic lactams, under iron catalysis, on three privileged motifs (i.e., the piperidine-, pyrrolidine-, and morpholine heterocycles) is described. The highlight of the studies is the strategic employment of a cheap iron precatalyst to achieve intramolecular dehydrative coupling, with complete stereofidelity. Our effortless ability to readily assemble 2-azabicyclic architectures using an environmentally benign approach that also features non benzylic tertiary alcohols, in a regiocontrolled, cost-effective, step-economical and modular manner, are some of the practical and conceptual advantages of the strategy over existing approaches.

We are confident that medicinal chemistry community will embrace the current work and find that it offers modular access to functionalized lactam-fused cyclopentenes bearing vicinal stereocenters.

 

We are grateful to Central Washington University for financial support through the donation of startup funds to T.K.B. H.B. is a recipient of the CWU COTS-SURE Fellowship and a Keck Scholar. K.H. is a Scottish Rite Scholar. S.L. is a Nelson Scholar and is also grateful to the Chemistry department for a graduate assistantship. Professor Blaise Dondji is thanked for initiating biological testing studies.

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