Diastereoselective Synthesis of Nitropyrrolizidines from Enantiopure exo- 4-Nitro-3,5-diphenylproline through 1,3-Dipolar Cycloadditions of non- Stabilized Azomethine Ylides
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Title: | Diastereoselective Synthesis of Nitropyrrolizidines from Enantiopure exo- 4-Nitro-3,5-diphenylproline through 1,3-Dipolar Cycloadditions of non- Stabilized Azomethine Ylides |
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Authors: | García-Mingüens, Eduardo | Nájera, Carmen | Sansano, Jose M. |
Research Group/s: | Síntesis Asimétrica (SINTAS) |
Center, Department or Service: | Universidad de Alicante. Departamento de Química Orgánica | Universidad de Alicante. Instituto Universitario de Síntesis Orgánica |
Keywords: | Pyrrolizidine | Nitroprolinates | Cycloaddition | Azomethine ylides | Decarboxylation | Multicomponent |
Knowledge Area: | Química Orgánica |
Issue Date: | 2018 |
Publisher: | Bentham Science Publishers |
Citation: | Letters in Organic Chemistry. 2018, 15(5): 431-440. doi:10.2174/1570178615666171221142214 |
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. |
Sponsor: | We gratefully acknowledge financial support from the Spanish Ministerio de Economía y Competitividad (MINECO) (projects CTQ2013-43446-P and CTQ2014-51912-REDC), the Spanish Ministerio de Economía, Industria y Competitividad, Agencia Estatal de Investigación (AEI) and Fondo Europeo de Desarrollo Regional (FEDER, EU) (projects CTQ2016-76782-P and CTQ2016-81797-REDC), the Generalitat Valenciana (PROMETEO2009/039 and PROMETEOII/2014/ 017) and the University of Alicante. |
URI: | http://hdl.handle.net/10045/74910 |
ISSN: | 1570-1786 (Print) | 1875-6255 (Online) |
DOI: | 10.2174/1570178615666171221142214 |
Language: | eng |
Type: | info:eu-repo/semantics/article |
Rights: | © 2018 Bentham Science Publishers |
Peer Review: | si |
Publisher version: | https://doi.org/10.2174/1570178615666171221142214 |
Appears in Collections: | INV - SINTAS - Artículos de Revistas |
Files in This Item:
File | Description | Size | Format | |
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2018_Garcia-Minguens_etal_LettOrgChem_final.pdf | Versión final (acceso restringido) | 2,14 MB | Adobe PDF | Open Request a copy |
2018_Garcia-Minguens_etal_LettOrgChem_accepted.pdf | Accepted Manuscript (acceso abierto) | 2,57 MB | Adobe PDF | Open Preview |
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