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Organocatalytic Asymmetric Michael-Hemiacetalization Reaction Between 2‑Hydroxyacetophenones and Enals: A Route to Chiral β,γ-Disubstituted γ‑Butyrolactones

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journal contribution
posted on 19.05.2017, 00:00 by Megha Balha, Buddhadeb Mondal, Subas Chandra Sahoo, Subhas Chandra Pan
The first highly enantioselective organocatalytic reaction employing 2-hydroxyacetophenones is disclosed, namely Michael-hemiacetalization reaction of 2-hydroxyacetophenones with enals. The combination of a primary amine and a secondary amine catalyst was found to be the best choice for this methodology. The products of this reaction were obtained in high enantio- and diastereoselectivities and were converted to a variety of biologically important γ-butyrolactones.

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