Diastereoselective Synthesis of Nitropyrrolizidines from Enantiopure exo- 4-Nitro-3,5-diphenylproline through 1,3-Dipolar Cycloadditions of non- Stabilized Azomethine Ylides

Title:Diastereoselective Synthesis of Nitropyrrolizidines from Enantiopure exo- 4-Nitro-3,5-diphenylproline through 1,3-Dipolar Cycloadditions of non- Stabilized Azomethine Ylides

Volume: 15 Issue: 5

Author(s): Eduardo Garcia-Minguens, Carmen Najera*Jose M. Sansano*

Affiliation:

• Departamento de Quimica Organica and Centro de Innovacion en Quimica Avanzada (ORFEO-CINQA), Facultad de Ciencias, Universidad de Alicante, 03080-Alicante,Spain

• Departamento de Quimica Organica and Centro de Innovacion en Quimica Avanzada (ORFEO-CINQA), Facultad de Ciencias, Universidad de Alicante, 03080-Alicante,Spain

Keywords: Pyrrolizidine, nitroprolinates, cycloaddition, azomethine ylides, decarboxylation, multicomponent.

Abstract: Enantiopure exo-4-nitro-3,5-diphenylproline reacts with aldehydes and electrophilic alkenes, in good yields, through a multicomponent 1,3-dipolar cycloaddition where the intermediate azomethine ylide is generated by the decarboxylative route. The reactions with maleimides afford diastereoselectively nitropyrrolizidines. Dimethyl fumarate and 1,2-bis(phenylsulfonyl)ethylene also give variable mixtures of diastereoisomeric nitropyrrolizidines. The replacement of aldehydes by phenyl-3-buten-2- one also affords satisfactory results with high diastereoselection although in lower yields. The stereochemical outcome is studied and defined according to the absolute configuration of the resulting cycloadducts.

Cite this article as:

Garcia-Minguens Eduardo , Najera Carmen *, Sansano M. Jose *, Diastereoselective Synthesis of Nitropyrrolizidines from Enantiopure exo- 4-Nitro-3,5-diphenylproline through 1,3-Dipolar Cycloadditions of non- Stabilized Azomethine Ylides, Letters in Organic Chemistry 2018; 15 (5) . https://dx.doi.org/10.2174/1570178615666171221142214