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Azetidines via Aza Paterno Buechi July 19th.pdf (1.34 MB)
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Functionalized Azetidines Via Visible Light-Enabled Aza Paternò-Büchi Reactions

preprint
revised on 19.07.2019 and posted on 22.07.2019 by Marc R. Becker, Alistair D. Richardson, Corinna S. Schindler

Azetidines are four-membered nitrogen-containing heterocycles that hold great promise in current medicinal chemistry due to their desirable pharmacokinetic effects. However, a lack of efficient synthetic methods to access functionalized azetidines has hampered their incorporation into pharmaceutical lead structures. As [2+2] cycloaddition reaction between imines and alkenes, the aza Paternò-Büchi reaction arguably represents the most direct approach to functionalized azetidines. Currently, competing reaction paths accessible upon photochemical excitation of the substrates greatly restrict the synthetic utility of these transformations. We herein report the development of a visible light-enabled aza Paternò-Büchi reaction that surmounts existing limitations and represents a general solution for the direct formation of functionalized azetidines from imine and alkene containing precursors.


Funding

R01-GM118644, Alfred P. Sloan Foundation, David and Lucile Packard Foundation, Camille and Henry Dreyfus Foundation

History

Email Address of Submitting Author

marcrb@umich.edu

Institution

University of Michigan

Country

United States

ORCID For Submitting Author

0000-0003-4259-6992

Declaration of Conflict of Interest

The authors declare no conflict of interest.

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