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

✍ Scribed by Sophie Faure; Sylvie Piva-Le Blanc; Olivier Piva

Publisher: Elsevier Science
Year: 1999
Tongue: French
Weight: 227 KB
Volume: 40
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(99)01173-9

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✦ Synopsis

Unsaturated oxoesters and amides have been submitted to cross-coupling metathesis with trimethylallylsilane using Grubbs' catalyst. The resulting allylsilanes 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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