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

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

Journal Name: Letters in Organic Chemistry

Volume 15 , Issue 5 , 2018

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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.

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Article Details

VOLUME: 15
ISSUE: 5
Year: 2018
Page: [431 - 440]
Pages: 10
DOI: 10.2174/1570178615666171221142214
Price: $58

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