期刊
ORGANIC LETTERS
卷 24, 期 24, 页码 -出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c01483
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资金
- National Institute of General Medical Sciences [R35-GM144286]
- University of Michigan
- University of Michigan's Rackham Merit Fellowship
- National Institutes of Health F31 Predoctoral Fellowship [5F31GM140677-02]
- American Cancer Society [PF-16-236-01CDD]
- Australian Governments Endeavour Leadership Fellowship
This article details the development of a photochemical reaction involving cyclopropylimines and substituted alkenes, which undergo a [3+2] cycloaddition to form aminocyclopentane derivatives. The use of a Schiff base enables a masked N-centered radical approach, which is activated upon excitation with visible light. The cycloaddition products can be directly converted to N-functionalized aminocyclopentanes through solvolysis and N-acylation. The photochemical component of this reaction has been demonstrated to be feasible in continuous flow.
Detailed herein is the development of a photo-chemical intermolecular formal [3+2] cycloaddition between cyclopropylimines and substituted alkenes to generate aminocyclopentane derivatives. The Schiff base 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 visible light. The cycloaddition products were directly converted to N-functionalized aminocyclopentanes via solvolysis and N-acylation. The photochemical component of this reaction sequence was demonstrated to operate in continuous flow.
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