Stereoselective Synthesis of Conjugated 2,4-Alkadienoates via the Palladium-Catalyzed Cross-Coupling of 1-Alkenylboronates with 3-Bromo-2-alkenoates
作者： Teiji Yanagi , Takayuki Oh-e , Norio Miyaura , Akira Suzuki
DOI: 10.1246/BCSJ.62.3892
关键词: Palladium 、 Aliphatic compound 、 Bicyclic molecule 、 Double bond 、 Coupling reaction 、 Stereoselectivity 、 Stereochemistry 、 Ferrocene 、 Medicinal chemistry 、 Cyclohexene 、 Chemistry 、 General chemistry
摘要: (2E,4E)-, (2Z,4E)-, and (2E,4Z)-2,4-Alkadienoates can be synthesized in high yields by the cross-coupling of ethyl (E)-3-bromoacrylate, methyl (E)-3-bromo-2-methylpropenoate, (Z)-3-bromocrotonate,1-bromo-2-(ethoxycarbonyl)cyclohexene, 4-bromocoumarin with 2-[(E)-1-alkenyl]-1,3,2-benzodioxaboroles or diisopropyl (Z)-1-hexenylboronate presence 3 mol% Pd(OAc)2, 6 PPh3, 2 equivalents Na2CO3 K2CO3 alcoholic solvents while retaining original configuration double bonds β-bromo esters 1-alkenylboronates. Although coupling reaction 1-hexenylboronate (Z)-3-bromoacrylate gave a mixture (2Z,4E)- (2E,4E)-nonadienoates ratio 63 : 37, it was found that use bis(diphenylphosphino)ferrocene as ligand palladium brought about stereoselective under mild conditions.
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