Diastereoselective multicomponent Amine-Aldehyde-Dienophile (AAD) process for the synthesis of polysubstituted cyclohex-2-enylamines

TETRAHEDRON

卷:75

Article

Selva, Veronica^1,2,3  Chabour, Ihssene^1,2,3  Najera, Carmen^1,2  Sansano, Jose M.^1,2,3 

[1] Univ Alicante, Fac Ciencias, Dept Quim Organ, E-03080 Alicante, Spain

[2] Univ Alicante, Fac Ciencias, Ctr Innovac Quim Avanzada ORFEO CINQA, E-03080 Alicante, Spain

[3] Univ Alicante, Fac Ciencias, Inst Sintesis Organ, E-03080 Alicante, Spain

关键词: Multicomponent;    AAD;    Cyclohex-2-enylamine;    Diels-Alder;    Primary amines;   

DOI  :  10.1016/j.tet.2019.01.063

来源: Elsevier

【 摘 要 】

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 MD 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. (C) 2019 Elsevier Ltd. All rights reserved.

【 授权许可】

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