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Experimental and Computational Studies Unraveling the Peculiarity of Enolizable Oxoesters in the Organocatalyzed Mannich-Type Addition to Cyclic N-Acyl Iminium Ions

1
Department of Pharmacy, University of Pisa, via Bonanno 33, 56126 Pisa, Italy
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Department of Chemistry and Industrial Chemistry, University of Pisa, via Moruzzi 3, 56124 Pisa, Italy
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Authors to whom correspondence should be addressed.
Molecules 2020, 25(8), 1903; https://doi.org/10.3390/molecules25081903
Received: 2 April 2020 / Revised: 15 April 2020 / Accepted: 17 April 2020 / Published: 20 April 2020
γ− and δ-Oxoesters are easily available starting materials that have been sparingly used in some organocatalyzed reactions proceeding with a high enantioselectivity. In our experimentation we found that the use of these compounds as the enolizable (nucleophilic) component in organocatalyzed Mannich-type reactions using in situ-generated cyclic N-acyl iminium ions gave low diastereoselectivity and low to moderate values of enantioselectivity. This significant drop of facial selectivity with respect to simple aliphatic aldehydes has been rationalized by means of density functional theory (DFT) calculations. View Full-Text
Keywords: N,O-acetals; organocatalysis; oxoesters; Mannich reactions; DFT study; heteroaryl lactones N,O-acetals; organocatalysis; oxoesters; Mannich reactions; DFT study; heteroaryl lactones
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MDPI and ACS Style

Menichetti, A.; Di Pietro, S.; Di Bussolo, V.; Favero, L.; Pineschi, M. Experimental and Computational Studies Unraveling the Peculiarity of Enolizable Oxoesters in the Organocatalyzed Mannich-Type Addition to Cyclic N-Acyl Iminium Ions. Molecules 2020, 25, 1903.

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