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Dr. Gokarneswar Sahoo, Dr. Hasibur Rahaman, Dr. Ádám Madarász, Dr. Imre Pápai, Mikko Melarto, Dr. Arto Valkonen and Prof. Dr. Petri M. Pihko Dihydrooxazine Oxides as Key Intermediates in Organocatalytic Michael Additions of Aldehydes to Nitroalkenes Angewandte Chemie International Edition 51

Version of Record online: 13 NOV 2012 | DOI: 10.1002/anie.201204833

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Pause and play: Dihydrooxazine oxides are stable intermediates that are protonated directly, without the intermediacy of the zwitterions, in organocatalytic Michael additions of aldehydes and nitroalkenes (see scheme, R=alkyl). Protonation of these species explains both the role of the acid co-catalyst in these reactions, and the observed stereochemistry when the reaction is conducted with α-alkylnitroalkenes.

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