Organocatalytic Activity of N-Heterocyclic Carbenes in the Michael Addition of 1,3-Dicarbonyls: Application to a Stereoselective Spirocyclization Sequence - CNRS - Centre national de la recherche scientifique Accéder directement au contenu
Article Dans Une Revue Advanced Synthesis and Catalysis Année : 2009

Organocatalytic Activity of N-Heterocyclic Carbenes in the Michael Addition of 1,3-Dicarbonyls: Application to a Stereoselective Spirocyclization Sequence

Thomas Boddaert
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Yoann Coquerel
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Jean Rodriguez
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Résumé

An eco-compatible diversity-oriented synthesis of a-spirolactones and a-spirolactams is described. The overall transformation involves an olefin cross-metathesis 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 carbine catalyst.

Dates et versions

hal-00678242 , version 1 (12-03-2012)

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Thomas Boddaert, Yoann Coquerel, Jean Rodriguez. Organocatalytic Activity of N-Heterocyclic Carbenes in the Michael Addition of 1,3-Dicarbonyls: Application to a Stereoselective Spirocyclization Sequence. Advanced Synthesis and Catalysis, 2009, 351, pp.1744-1748. ⟨10.1002/adsc.200900292⟩. ⟨hal-00678242⟩
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