Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 351, Issue 11-12, Pages 1744-1748Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.200900292
Keywords
cross metathesis; Michael addition; N-heterocyclic carbenes; organocatalysis; spiro compounds
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An eco-compatible diversity-oriented synthesis of alpha-spirolactones and alpha-spirolactams is described. The overall transformation involves an olefin cross-meta thesis followed by an intramolecular organocatalytic Michael-induced spirocyclization. Under microwave irradiation, the Hoveyda-Grubbs precatalyst can be iteratively used as the source of both the metathesis ruthenium-based catalyst, and the spirocyclization N-heterocyclic carbene catalyst.
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