ChemInform Abstract: Dihydrooxazine Oxides as Key Intermediates in Organocatalytic Michael Additions of Aldehydes to Nitroalkenes.

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RESEARCH PRODUCT

ChemInform Abstract: Dihydrooxazine Oxides as Key Intermediates in Organocatalytic Michael Additions of Aldehydes to Nitroalkenes.

Gokarneswar Sahoo Mikko Melarto ÁDám Madarász Hasibur Rahaman Petri M. Pihko Imre Pápai Arto Valkonen

subject

chemistry.chemical_classification Addition reaction Chemistry Organocatalysis Protonation General Medicine Medicinal chemistry Alkyl

description

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.

year	journal	country	edition	language
2013-04-25	ChemInform

https://doi.org/10.1002/chin.201320082

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