title: Highly Efficient Catalytic Formation of (Z)-1,4-But-2-ene Diols Using Water as a Nucleophile.
abstract: The first general catalytic and highly stereoselective formation of (Z)-1,4-but-2-ene diols is described from readily available and modular vinyl-substituted cyclic carbonate precursors using water as a nucleophilic reagent. These 1,4-diol scaffolds can be generally prepared in high yields and with ample scope in reaction partners using a simple synthetic method that does not require the presence of any additive or any special precaution unlike the stoichiometric approaches reported to date. Control experiments support the mechanistic view that hyperconjugation within the catalytic intermediate after decarboxylation plays an imperative role to control the stereoselective outcome of these reactions.
authors.affiliation: Institute of Chemical Research of Catalonia (ICIQ), The Barcelona Institute of Science and Technology, Av. Països Catalans 16, 43007, Tarragona, Spain.
authors.forename: Wusheng
authors.initials: W
authors.lastname: Guo
authors.affiliation: Institute of Chemical Research of Catalonia (ICIQ), The Barcelona Institute of Science and Technology, Av. Països Catalans 16, 43007, Tarragona, Spain.
authors.forename: Luis
authors.initials: L
authors.lastname: Martínez-Rodríguez
authors.affiliation: Institute of Chemical Research of Catalonia (ICIQ), The Barcelona Institute of Science and Technology, Av. Països Catalans 16, 43007, Tarragona, Spain.
authors.forename: Eddy
authors.initials: E
authors.lastname: Martin
authors.affiliation: Institute of Chemical Research of Catalonia (ICIQ), The Barcelona Institute of Science and Technology, Av. Països Catalans 16, 43007, Tarragona, Spain.
authors.forename: Eduardo C
authors.initials: EC
authors.lastname: Escudero-Adán
authors.affiliation: Institute of Chemical Research of Catalonia (ICIQ), The Barcelona Institute of Science and Technology, Av. Països Catalans 16, 43007, Tarragona, Spain. akleij@iciq.es.|Catalan Institute of Research and Advanced Studies (ICREA), Pg. Lluís Companys 23, 08010, Barcelona, Spain. akleij@iciq.es.
authors.forename: Arjan W
authors.identifier: 0000-0002-7402-4764
authors.initials: AW
authors.lastname: Kleij
keywords: But-2-ene diols; decarboxylative functionalization; homogeneous catalysis; palladium; stereoselectivity