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Regio‐ and Stereoselective Preparation of β,γ‐Unsaturated Carboxylic Acids by One‐Pot Sequential Double 1,6‐Addition of Grignard Reagents to Methyl Coumalate
Author(s) -
Plevová Kristína,
Chang Liang,
Martin Emmeline,
Llopis Quentin,
Dechoux Luc,
Thorimbert Serge
Publication year - 2016
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201600212
Subject(s) - stereoselectivity , reagent , chemistry , grignard reagent , metal , organic chemistry , combinatorial chemistry , stereochemistry , catalysis
An efficient regio‐ and stereoselective metal‐catalyzed addition of two Grignard reagents (homo‐coupling, 2 RMgX or hetero‐coupling, R 1 MgX+R 2 MgX) to methyl coumalate (methyl 2‐oxo‐2 H ‐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.