Synthesis of vinyl spirolactones and lactams by sequential cross-coupling metathesis, [2+2] photocycloaddition and cyclobutane ring-opening

Add time:08/07/2019    Source:sciencedirect.com

Unsaturated oxoesters and amides have been submitted to cross-coupling metathesis with trimethylallylsilane using Grubbs' catalyst. The resulting allysilanes underwent, under irradiation, intramolecular [2+2] photocycloaddition leading to trimethylsilylmethylcyclobutanes. By treatment with an appropriate Lewis acid, vinyl spiranic lactones and lactams were isolated in good yields.

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