1,3-Dipolar cycloadditions using catalysts with double chirality and novel multicomponent [4+2] processes

  1. Chabour, ihssene
Dirigida por:
  1. Jose M. Sansano Gil Director
  2. Carmen Nájera Domingo Codirectora

Universidad de defensa: Universitat d'Alacant / Universidad de Alicante

Fecha de defensa: 08 de febrero de 2021

Tribunal:
  1. H.Q. Nimal Gunaratne Presidente/a
  2. Francisco Foubelo García Secretario
  3. Uxue Uria Pujana Vocal
Departamento:
  1. QUIMICA ORGANICA

Tipo: Tesis

Teseo: 647921 DIALNET lock_openRUA editor

Resumen

In this thesis, different cycloaddition reactions, such as the enantioselective 1,3-dipolar-cycloaddition, which takes place between in situ generated stabilized azomethine ylides, and electrophilic alkenes, and the diastereoselective multicomponent reactions Amine-Aldehyde-Dienophile (AAD) or Phosphoramidate-Aldehyde-Dienophile (PAD) are described. In Chapter 1, an asymmetric 1,3-dipolar cycloaddition reaction involving an imino ester with tert-butyl acrylate was carried out using a silver(I) complex with double chirality, formed from a chiral phosphoramidite and chiral silver binolphosphate(I). The goal of this reaction is to synthesize key enantiomerically enriched structures to access the GSK-third generation of HCV inhibitors. In Chapter 2, the synthesis of polysubstituted cyclohex-2-enylamines using the multicomponent Amine-Aldehyde-Dienophile reaction involving benzyl or 4-methoxybenzylamine, is described. The study the diastereoselective version, employing commercially available chiral benzylic amines, or even a maleimide with the chiral information at the nitrogen atom, are also reported. In Chapter 3, the synthesis of polysubstituted cyclohex-2-enylamines derivatives using the multicomponent Phosphoramidate-Aldehyde-Dienophile (PAD), is described. Several series of N-substituted phosphoramidates reacted with α,β-unsaturated aldehydes, bearing hydrogen atoms at the γ-position, in good yields.