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Programmable late-stage functionalization of bridge-substituted bicyclo[1.1.1]pentane bis-boronates

https://doi.org/10.1038/s41557-023-01342-7

Yang, Yangyang; Tsien, Jet; Dykstra, Ryan; Chen, Si-Jie; Wang, James B.; Merchant, Rohan R.; Hughes, Jonathan M.; Peters, Byron K.; Gutierrez, Osvaldo; Qin, Tian (February 2024, Nature Chemistry)

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Enantioenriched BCP Benzylamine Synthesis via Metal Hydride Hydrogen Atom Transfer/Sulfinimine Addition to [1.1.1]Propellane

https://doi.org/10.1021/acs.orglett.1c03681

Shelp, Russell; Merchant, Rohan R.; Hughes, Jonathan M.; Walsh, Patrick J. (January 2022, Organic Letters)

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Strain-release 2-azaallyl anion addition/borylation of [1.1.1]propellane: synthesis and functionalization of benzylamine bicyclo[1.1.1]pentyl boronates

https://doi.org/10.1039/D1SC01349A

Shelp, Russell A.; Ciro, Anthony; Pu, Youge; Merchant, Rohan R.; Hughes, Jonathan M.; Walsh, Patrick J. (May 2021, Chemical Science)
null (Ed.)
We report a 3-component reaction between N -benzyl ketimines, [1.1.1]propellane, and pinacol boronates to generate benzylamine bicyclo[1.1.1]pentane (BCP) pinacol boronates. These structures are analogous to highly sought diarylmethanamine cores, which are common motifs in bioactive molecules. We demonstrate the versatility of the boronate ester handle via downstream functionalization through a variety of reactions, including a challenging Pd-catalyzed (hetero)arylation that exhibits a broad substrate scope. Together, these methods enable the synthesis of high-value BCP benzylamines which are inaccessible by existing methods. Furthermore, we demonstrate the successful application of these newly developed (hetero)arylation conditions to a variety of challenging tertiary pinacol boronates, including nitrogen-containing heterocycles, 1,1-disubstituted cyclopropanes, and other BCP cores.
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