Diastereoselective multicomponent phosphoramidate-aldehyde-dienophile (PAD) process for the synthesis of polysubstituted cyclohex-2-enyl-amine derivatives
| Autor: | José M. Sansano, Carmen Nájera, Ihssene Chabour |
|---|---|
| Přispěvatelé: | Universidad de Alicante. Departamento de Química Orgánica, Universidad de Alicante. Instituto Universitario de Síntesis Orgánica, Síntesis Asimétrica (SINTAS) |
| Jazyk: | angličtina |
| Rok vydání: | 2020 |
| Předmět: |
chemistry.chemical_classification
Allylic rearrangement 010405 organic chemistry Organic Chemistry Diels-Alder Multicomponent Phosphoramidate Conjugated system 010402 general chemistry 01 natural sciences Biochemistry Aldehyde PAD 0104 chemical sciences chemistry.chemical_compound Hydrolysis Química Orgánica chemistry Cyclohex-2-enylamine Drug Discovery Functional group Primary amines Organic chemistry Amine gas treating Maleimide |
| Zdroj: | RUA. Repositorio Institucional de la Universidad de Alicante Universidad de Alicante (UA) |
| Popis: | 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 α,β-unsaturated aldehydes bearing hydrogens at the γ-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. We gratefully acknowledge financial support from the Spanish Ministerio de Economía y Competitividad (MINECO), Agencia Estatal de Investigaci on (AEI) and Fondo Europeo de Desarrollo Regional (FEDER, EU) (Project Nos. CTQ2013-43446-P, CTQ2014-51912-REDC, CTQ2016-76782-P, CTQ2016-81797-REDC, CTQ2016-81893REDT, and CTQ2016-76155-R), the Generalitat Valenciana (PROMETEOII/2014/017) and the University of Alicante. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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