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Electron Donor-Acceptor Complex-Driven Divergent Routes to α-Amino Bicyclopentyl Iodides and Methylene Cyclobutanols. | LitMetric

Amines are essential due to their structural diversity and biological significance. Introducing the valuable bicyclopentane (BCP) moiety at the α-position of amines offers a promising strategy for developing novel bioactive compounds. This study outlines a divergent synthesis approach to generate α-amino-functionalized bicyclopentyl iodides and methylene cyclobutanols under mild and environmentally sustainable conditions. By employing an electron donor-acceptor (EDA) complex between amine and the inexpensive and readily available inorganic base CsCO, this method circumvents the need for strongly reducing, metal-based photocatalysts typically required for aryl radical generation. This approach enables the α-functionalization of various aliphatic and alicyclic amines a 1,5-hydrogen atom transfer mechanism.

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http://dx.doi.org/10.1021/acs.orglett.4c03913DOI Listing

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