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

Authors :: Ghisu, Lorenza
Melis, Nicola
Secci, Francesco
Frongia, Angelo
Source :: Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry. Nov2015, Vol. 56 Issue 46, p6409-6412. 4p.
Publication Year :: 2015
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. [ABSTRACT FROM AUTHOR]

Subjects :: *STEREOSELECTIVE reactions
*MICHAEL reaction
*CYCLOHEXENE
*INTRAMOLECULAR catalysis
*PROTONATION constants
*ANILINE

Language :: English
ISSN :: 00404039
Volume :: 56
Issue :: 46
Database :: Academic Search Index
Journal :: Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry
Publication Type :: Academic Journal
Accession number :: 110576486
Full Text :: https://doi.org/10.1016/j.tetlet.2015.09.138

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