Angewandte Chemie - International Edition p. 17297 - 17300 (2020)
Update date:2022-08-04
Topics:
Bowers, Bekah E.
Gagné, Michel R.
Lowe, Jared M.
Seo, Youngran
Controlling which products one can access from the predefined biomass-derived sugars is challenging. Changing from CH2Cl2 to the greener alternative toluene alters which C?O bonds in a sugar are cleaved by the tris(pentafluorophenyl)borane/HSiR3 catalyst system. This increases the diversity of high-value products that can be obtained through one-step, high-yielding, catalytic transformations of the mono-, di-, and oligosaccharides. Computational methods helped identify this non-intuitive outcome in low dielectric solvents to non-isotropic electrostatic enhancements in the key ion pair intermediates, which influence the reaction coordinate in the reactivity-/selectivity-determining step. Molecular-level models for these effects have far-reaching consequences in stereoselective ion pair catalysis.
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