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A One Pot Photochemical Method for the Generation of Functionalized Aminocyclopentanes

preprint
submitted on 12.10.2020, 13:41 and posted on 13.10.2020, 10:13 by Madison Sowden, James L. Collins III, Daryl Staveness, Corey Stephenson
Detailed herein is the development of a photochemical intermolecular formal [3+2] cycloaddition between cyclopropylimines and substituted alkenes to generate cyclopentylimines. The Schiff base auxiliary of the cyclopropylimine was designed to enable a masked N-centered radical approach in which the requisite open-shell character was achieved upon excitation with violet light. The cycloaddition products were directly converted to N-functionalized aminocyclopentanes via N-acylation and solvolysis, thus offering a three-step, one-pot procedure for the production of diversely-substituted aminocyclopentanes. The photochemical component of this reaction sequence was demonstrated to operate in continuous flow and was amenable to gram-scale production.

Funding

Photochemical synthesis of bioactive molecules

National Institute of General Medical Sciences

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History

Email Address of Submitting Author

crjsteph@umich.edu

Institution

University of Michigan

Country

USA

ORCID For Submitting Author

0000-0002-2443-5514

Declaration of Conflict of Interest

None

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