Highly Efficient Catalytic Formation of (Z)‐1, 4‐But‐2‐ene Diols Using Water as a Nucleophile. (16th August 2016)

• Record Type: Journal Article
• Authors: Guo, Wusheng; Martínez‐Rodríguez, Luis; Martin, Eddy; Escudero‐Adán, Eduardo C.; Kleij, Arjan W.
• Is Part Of: Angewandte Chemie. Volume 128:Number 37(2016)
• Page Start: 11203
• Page End: 11206
• Publication Date: 2016-08-16
• Subjects: But-2-endiole -- Decarboxylierende Funktionalisierung -- Homogene Katalyse -- Palladium -- Stereoselektivität; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201603638
• Languages: English
• ISSNs: 0044-8249

Abstract

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.