Regio- and stereoselective synthesis of novel isoxazolidine heterocycles by 1,3-dipolar cycloaddition between C-phenyl-N-methylnitrone and substituted alkenes. Experimental and DFT investigation of selectivity and mechanism-Reference-Cited by-同舟云学术

Regio- and stereoselective synthesis of novel isoxazolidine heterocycles by 1,3-dipolar cycloaddition between C-phenyl-N-methylnitrone and substituted alkenes. Experimental and DFT investigation of selectivity and mechanism

Published:2017 Issue:48 Volume:7 Page:30128-30141
ISSN:2046-2069
Container-title:RSC Advances
language:en
Short-container-title:RSC Adv.

Author:

Hellel Djamila¹²³⁴⁵,Chafaa Fouad¹²³⁴⁵,Khorief Nacereddine Abdelmalek¹²³⁴⁵^ORCID,Djerourou Abdelhafid¹²³⁴⁵,Vrancken Emmanuel⁶⁷⁸⁹¹⁰

Affiliation:

1. Laboratoire de Synthèse et Biocatalyse Organique

2. Département de Chimie

3. Faculté des Sciences

4. Université Badji Mokhtar Annaba

5. 23000 Annaba

6. Institut Charles Gerhardt

7. UMR 5253 CNRS-UM2-UM1 ENSCM

8. Laboratoire Architectures Moléculaires et Matériaux Nanostructurés (AM2N)

9. Ecole Nationale Supérieure de Chimie de Montpellier

10. 34296 Montpellier

Abstract

A series of isoxazolidine heterocycles was synthesized through the 1,3-dipolar cycloaddition (13DC) reaction of C-phenyl-N-methylnitrone with different substituted alkenes.

Publisher

Royal Society of Chemistry (RSC)

Subject

General Chemical Engineering,General Chemistry

Link

http://pubs.rsc.org/en/content/articlepdf/2017/RA/C7RA00258K

Reference52 articles.

1. R. Huisgen , in 1,3-Dipolar Cycloaddition Chemistry, ed. A. Padwa, John Wiley & Sons, New York, 1984, vol. 1, pp. 42–47

2. J. N. Martin and R. C.Jons, Nitrones, in Synthetic Applications of 1,3-Dipolar Cycloaddition. Chemistry Towards Heterocycles and Natural Products, ed. A. Padwa and W. H. Pearson, John Wiley & Sons, Hoboken, NJ, 2003, ch. 1

3. Optically active isoxazolidines via asymmetric cycloaddition reactions of nitrones with alkenes: applications in organic synthesis

4. Asymmetric 1,3-Dipolar Cycloaddition Reactions

5. 1,3-Dipolar cycloaddition reactions of nitrones with alkyl vinyl ethers catalyzed by chiral oxazaborolidines

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