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Exploration of a Novel, Enamine-Solid-Base Catalyzed Aldol Condensation with C‑Glycosidic Pyranoses and Furanoses

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journal contribution
posted on 27.07.2018, 00:00 authored by Tamara M. de Winter, Yanna Balland, Arwen Evenstar Neski, Laurène Petitjean, Hanno C. Erythropel, Magali Moreau, Julien Hitce, Philip Coish, Julie B. Zimmerman, Paul T. Anastas
A variety of unprotected C-glycosidic ketones were employed in a novel enamine-solid-base catalyzed (ESBC) aldol condensation to expand the scope and scalability of a previously reported reaction. The starting ketones were obtained from unprotected pyranoses and furanoses following Lubineau’s method via a Knoevenagel condensation. The aldol condensation reaction of the C-glycosidic ketones was performed with a nontoxic and abundant amino acid, L-proline, along with magnesium oxide (MgO) as a recyclable and sustainable catalyst. The enamine-solid-base catalyzed aldol condensations provided the corresponding (E)-α,β-unsaturated ketones in excellent isolated yields (91–100%).

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