α-Hydroxyacids accelerate the Diels-Alder reaction of dibutyl vinylboronate with cyclopentadiene: experimental results and mechanistic insightsElectronic supplementary information (ESI) available: General experimental procedures; 11B NMR spectra; computational methods; coefficients, shapes and energies of the FMOs of the reactants; optimized geometries of transition structures not included in the paper; Cartesian coordinates, absolute energies including zero-point energy corrections, free energi

• Main Authors: Grimblat, N, Sarotti, A. M, Pisano, P. L, Pellegrinet, S. C
• Format: Journal Article
• Published: 07.03.2016
• ISSN: 1144-0546; 1369-9261
• DOI: 10.1039/c5nj03015c

We have found that α-hydroxyacids accelerate the Diels-Alder reaction of dibutyl vinylboronate with cyclopentadiene. When stoichiometric quantities are used, excellent yields are obtained, while catalytic activities are moderate. DFT calculations suggested that the activation of the dienophile occurs by ligand exchange with both functionalities of the α-hydroxyacid. Dibutyl vinylboronate reacts with cyclopentadiene under mild conditions in the presence of ( S )-mandelic acid probably via an activated dioxaborolane intermediate.