Stereoselective aza-Michael addition of anilines to 1-nitro cyclohexene by intramolecular protonation

GHISU, LORENZA;MELIS, NICOLA;SECCI, FRANCESCO;FRONGIA, ANGELO

2015-01-01

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Abstract

An asymmetric synthesis of α-aryl amino-β-nitro cyclohexanes has been achieved by means of a tandem aza-Michael addition-protonation reaction starting from 1-nitro cyclohexene and anilines. The transformation is proposed to proceed via a transient nitrile enolate which is subsequently stereoselectively protonated by an intramolecular transfer of the proton from nitrogen to the nitronate α-carbon.