Diastereoselective multicomponent Amine-Aldehyde-Dienophile (AAD) process for the synthesis of polysubstituted cyclohex-2-enylamines |
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| Authors: | Verónica Selva Ihssene Chabour Carmen Nájera José M. Sansano |
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| Affiliation: | 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 |
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| 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. |
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| Keywords: | Multicomponent AAD Cyclohex-2-enylamine Diels-Alder Primary amines |
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