A Ni-Al bimetallic catalyzed enantioselective cycloaddition reaction of cyclopropyl carboxamides with alkynes has been developed. A series of cyclopentenyl carboxamides were obtained in up to 99% yield and 94% ee. The bifunctional-ligand-enabled bimetallic catalysis proved to be an efficient strategy for the C-C bond cleavage of unreactive cyclopropanes.
Bicyclo[1.1.1]pentanes (BCPs) have sparked the interest of medicinal chemists due to their recent discovery as bioisosteres of aromatic rings.T os tudy the biological activity of this relatively new class of bioisosteres,r eliable methods to incorporate BCPs into target molecules are in high demand, as reflected by af lurry of methods for BCP synthesis in recent years.I nt his work, we disclose ag eneral method for the synthesis of BCP-containing dithianes which,u pon deprotection, provide access to BCP analogues of medicinally abundant diarylketones.Abroad scope of 2-aryl-1,3-dithianes,including several heterocyclic derivatives,react with [1.1.1]propellane to afford2 6n ew derivatives in good to excellent yields.F urther transformation of the dithiane portion into av ariety of functional groups demonstrates the robustness of the products. Acomputational study indicates that the reaction of 2-aryl-1,3dithianes and [1.1.1]propellane proceeds via at wo-electron pathway.Scheme 1. Previous synthesis of BCP ketones, examples of bioactive diaryl ketones, general reactivity of dithianes, and synthesis of BCP dithianes.
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 after diarylmethanamine cores, which...
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