Dihydrooxazine oxides as key intermediates in organocatalytic Michael additions of aldehydes to nitroalkenes.

نویسندگان

  • Gokarneswar Sahoo
  • Hasibur Rahaman
  • Adám Madarász
  • Imre Pápai
  • Mikko Melarto
  • Arto Valkonen
  • Petri M Pihko
چکیده

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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عنوان ژورنال:
  • Angewandte Chemie

دوره 51 52  شماره 

صفحات  -

تاریخ انتشار 2012