AI Article Synopsis
- A new method is introduced for the rhodium-catalyzed transformation of hydroxyisoindolinone using vinylene carbonate, leading to the creation of unique spirolactams.
- The vinylene carbonate acts as a vinyl-oxygen cyclic synthon, allowing for direct transfer of C-H bonds to spiroheterocycle structures.
- The process is eco-friendly, producing only water (HO) and carbon monoxide (CO) as byproducts, making it compatible with green chemistry principles.
Article Abstract
Herein, a novel organic transformation involving rhodium-catalyzed divergent dehydroxylation/alkenylation of hydroxyisoindolinone with vinylene carbonate is reported, and a series of architecturally rigid and widely used spirolactams are obtained with excellent functional group tolerance and high selectivity. Remarkably, the promising vinylene carbonate reagent presents a distinct chemical reactivity as a vinyl-oxygen cyclic synthon and first transfers the C-H bond to spiroheterocycle scaffolds. Moreover, another chemoselectivity, direct dehydrogenative coupling with vinylene carbonate, is also presented. This protocol is compatible with green chemistry and only releases HO and CO as byproducts.
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| http://dx.doi.org/10.1039/d3cc03760f | DOI Listing |
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