Diastereoselective multicomponent phosphoramidate-aldehyde-dienophile (PAD) process for the synthesis of polysubstituted cyclohex-2-enyl-amine derivatives

TETRAHEDRON

卷:76

Article

Chabour, Ihssene^1,2,3  Najera, Carmen¹  Sansano, Jose M.^1,2,3 

[1] Univ Alicante, Fac Ciencias, Ctr Innovac Quim Avanzada ORFEO CINQA, Alicante 03080, Spain

[2] Univ Alicante, Fac Ciencias, Dept Quim Organ, Alicante 03080, Spain

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

关键词: Multicomponent;    PAD;    Cyclohex-2-enylamine;    Diets-Alder;    Primary amines;   

DOI  :  10.1016/j.tet.2019.130801

来源: Elsevier

【 摘 要 】

The reaction of diethyl phosphoramidate, conjugated aldehydes and maleimides takes place in a multicomponent sequence named phosphoramidate-aldehyde-dienophile (PAD). The reaction affords a series of N-substituted phosphoramidates in good yields with alpha,beta-unsaturated aldehydes bearing hydrogens at the gamma-position. The reaction is diastereoselective and the effect of chiral information in the maleimide is evaluated. A mechanism is also postulated and the feasible hydrolysis of the phosphoramidate functional group is achieved although the final allylic amine is difficult to isolate. (C) 2019 Published by Elsevier Ltd.

【 授权许可】

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