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Combination of Rearrangement with Metallic and Organic Catalyses: a Step- and Atom-economical Approach to alpha-Spirolactones and -lactams

Thomas Boddaert 1 Yoann Coquerel 1, * Jean Rodriguez 1, * 
* Corresponding author
1 STeRéO
ISM2 - Institut des Sciences Moléculaires de Marseille
Abstract : A general synthetic route to α-spirolactones and -lactams from 2-diazo-1,3-dicarbonyl compounds, (homo)allylic alcohols or amines and acrylic derivatives, involving a single consecutive reaction consisting of a Wolff rearrangement/α-oxo ketene trapping/cross metathesis/Michael addition sequence is described. During the consecutive reaction optimization, the organocatalytic activity of N,N-diaryl-1,3-imidazol(in)-2-ylidene N-heterocyclic carbenes (NHCs) in the Michael addition of 1,3-dicarbonyl compounds was discovered. A conceptually attractive version of the consecutive reaction was then developed, involving the Grubbs-Hoveyda ruthenium-based precatalyst containing the SIMes [1,3-bis(2,4,6-trimethylphenyl)imidazolin-2-ylidene] NHC ligand as the source of both the organometallic catalyst of the cross metathesis and the organic catalyst of the intramolecular Michael addition.
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https://hal.archives-ouvertes.fr/hal-00678227
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Submitted on : Monday, March 12, 2012 - 11:07:21 AM
Last modification on : Tuesday, December 14, 2021 - 8:36:12 AM

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Thomas Boddaert, Yoann Coquerel, Jean Rodriguez. Combination of Rearrangement with Metallic and Organic Catalyses: a Step- and Atom-economical Approach to alpha-Spirolactones and -lactams. European Journal of Organic Chemistry, Wiley-VCH Verlag, 2011, pp.5061-5070. ⟨10.1002/ejoc.201100734⟩. ⟨hal-00678227⟩

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