Regio- and Stereoselective Preparation of β,γ-Unsaturated Carboxylic Acids by One-Pot Sequential Double 1,6-Addition of Grignard Reagents to Methyl Coumalate - Sorbonne Université Accéder directement au contenu
Article Dans Une Revue Advanced Synthesis and Catalysis Année : 2016

Regio- and Stereoselective Preparation of β,γ-Unsaturated Carboxylic Acids by One-Pot Sequential Double 1,6-Addition of Grignard Reagents to Methyl Coumalate

Résumé

An efficient regio- and stereoselective metal-catalyzed addition of two Grignard reagents (homo-coupling, 2 RMgX or hetero-coupling, R1MgX+R2MgX) to methyl coumalate (methyl 2-oxo-2H-pyran-5-carboxylate) is described. This synthetic approach opens the access to a wide variety of functionalized β,γ-unsaturated carboxylic acids in a modular way. Control of the chemo- and stereoselectivity of this one-pot procedure is discussed.
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Dates et versions

hal-01366439 , version 1 (14-09-2016)

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Kristína Plevová, Liang Chang, Emmeline Martin, Quentin Llopis, Luc Dechoux, et al.. Regio- and Stereoselective Preparation of β,γ-Unsaturated Carboxylic Acids by One-Pot Sequential Double 1,6-Addition of Grignard Reagents to Methyl Coumalate. Advanced Synthesis and Catalysis, 2016, 358 (20), pp.3293-3297 ⟨10.1002/adsc.201600212⟩. ⟨hal-01366439⟩
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