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Diastereoselective multicomponent Amine-Aldehyde-Dienophile (AAD) process for the synthesis of polysubstituted cyclohex-2-enylamines
Authors:Verónica Selva  Ihssene Chabour  Carmen Nájera  José M Sansano
Institution:1. Departamento de Química Orgánica and Centro de Innovación en Química Avanzada (ORFEO-CINQA), Facultad de Ciencias, Universidad de Alicante, 03080, Alicante, Spain;2. Instituto de Síntesis Orgánica, Facultad de Ciencias, Universidad de Alicante, 03080, Alicante, Spain
Abstract:The multicomponent Amine-Aldehyde-Dienophile reaction is optimized employing benzyl or 4-methoxybenzylamine. The interest of the transformation consist in the synthesis of polysubstituted cyclohex-2-enylamines. The study of the scope of this AAD process is carried out, as well as the diastereoselective version, employing commercially available chiral benzylic amines and a maleimide with the chiral information at the N-substituent. VCD spectroscopy is a very useful tool for the determination of the absolute configuration of the isolated enantiomerically enriched compounds.
Keywords:Multicomponent  AAD  Cyclohex-2-enylamine  Diels-Alder  Primary amines
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