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A One Pot Photochemical Method for the Generation of Functionalized Aminocyclopentanes

preprint
submitted on 12.10.2020 and posted on 13.10.2020 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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