Asymmetric aza-Henry reactions from N-p-tolylsulfinylimines.
[reaction: see text] N-Sulfinylimines derived from aromatic or aliphatic aldehydes and ketones react with nitromethane and NaOH in a highly diastereoselective manner under mild conditions. In the presence of TBAF, the reaction rates are strongly increased and the stereoselectivity is inverted. This method provides enantiomerically pure beta-nitroamines derived from enolizable aldimines and ketimines, which so far are hardly accessible by aza-Henry reactions.
García Ruano
José Luis
JL
Departamento de Química Orgánica, Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid, Spain. joseluis.garcia.ruano@uam.es
Topp
Markus
M
López-Cantarero
Jesús
J
Alemán
José
J
Remuiñán
Modesto J
MJ
Cid
M Belén
MB