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

[ Vol. 15 , Issue. 5 ]

Author(s):

Eduardo Garcia-Minguens, Carmen Najera* and Jose M. Sansano*   Pages 431 - 440 ( 10 )

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.

Keywords:

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

Affiliation:

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

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