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Dihydrooxazine Oxides as Key Intermediates in Organocatalytic Michael Additions of Aldehydes to Nitroalkenes
Author(s) -
Sahoo Gokarneswar,
Rahaman Hasibur,
Madarász Ádám,
Pápai Imre,
Melarto Mikko,
Valkonen Arto,
Pihko Petri M.
Publication year - 2012
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201204833
Subject(s) - protonation , chemistry , catalysis , organocatalysis , michael reaction , organic chemistry , reaction intermediate , alkyl , reactive intermediate , medicinal chemistry , ion , enantioselective synthesis
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.