Stereoselective aza-Michael addition of anilines to 1-nitro cyclohexene by intramolecular protonation. Issue 46 (18th November 2015)

• Record Type: Journal Article
• Authors: Ghisu, Lorenza; Melis, Nicola; Secci, Francesco; Frongia, Angelo
• Is Part Of: Tetrahedron letters. Volume 56:Issue 46(2015)
• Page Start: 6409
• Page End: 6412
• Publication Date: 2015-11-18
• Subjects: Aza-Michael addition -- Asymmetric protonation -- Catalyst-free reactions -- Amines -- Organocatalysis; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2015.09.138
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: 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.