Display options
Cite
Floresta G, Talotta C, Gaeta C, et al. γ-Cyclodextrin as a Catalyst for the Synthesis of 2-Methyl-3,5-diarylisoxazolidines in Water. J Org Chem. 2017;82(9):4631-4639doi: 10.1021/acs.joc.7b00227.
Floresta, G., Talotta, C., Gaeta, C., De Rosa, M., Chiacchio, U., Neri, P., & Rescifina, A. (2017). γ-Cyclodextrin as a Catalyst for the Synthesis of 2-Methyl-3,5-diarylisoxazolidines in Water. The Journal of organic chemistry, 82(9), 4631-4639. https://doi.org/10.1021/acs.joc.7b00227
Floresta, Giuseppe, et al. "γ-Cyclodextrin as a Catalyst for the Synthesis of 2-Methyl-3,5-diarylisoxazolidines in Water." The Journal of organic chemistry vol. 82,9 (2017): 4631-4639. doi: https://doi.org/10.1021/acs.joc.7b00227
Floresta G, Talotta C, Gaeta C, De Rosa M, Chiacchio U, Neri P, Rescifina A. γ-Cyclodextrin as a Catalyst for the Synthesis of 2-Methyl-3,5-diarylisoxazolidines in Water. J Org Chem. 2017 May 05;82(9):4631-4639. doi: 10.1021/acs.joc.7b00227. Epub 2017 Apr 25. PMID: 28406307.
Copy Download .nbib Format: NLM
Share it on

J Org Chem. 2017 May 05;82(9):4631-4639. doi: 10.1021/acs.joc.7b00227. Epub 2017 Apr 25.

γ-Cyclodextrin as a Catalyst for the Synthesis of 2-Methyl-3,5-diarylisoxazolidines in Water.

The Journal of organic chemistry

Giuseppe Floresta, Carmen Talotta, Carmine Gaeta, Margherita De Rosa, Ugo Chiacchio, Placido Neri, Antonio Rescifina

Affiliations

  1. Dipartimento di Scienze del Farmaco, Università di Catania , Viale Andrea Doria 6, 95125 - Catania, Italy.
  2. Dipartimento di Scienze Chimiche, Università di Catania , Viale Andrea Doria 6, 95125 - Catania, Italy.
  3. Dipartimento di Chimica e Biologia "A. Zambelli", Università di Salerno , Via Giovanni Paolo II 132, 84084 - Fisciano (SA), Italy.

PMID: 28406307 DOI: 10.1021/acs.joc.7b00227

Abstract

A green and efficient 1,3-dipolar cycloaddition of nitrones with different styrenes and cinnamates using a catalytic amount of γ-cyclodextrin (γ-CD) in water has been developed to give substituted isoxazolidines. γ-CD was found to be highly efficacious in carrying out this reaction under an eco-friendly environment, affording moderate to excellent yields and, in some cases, excellent diastereomeric excess (up to >95%) at 100 °C in 8-12 h. The catalyst can be easily recuperated and recycled for several times without loss of activity. Water, an eco-friendly reaction medium, has been utilized for the first time, to the best of our knowledge, in this reaction. The credit of the presented protocol includes high yields and catalyst reusability, and precludes the use of organic solvents. The use of in silico calculations allowed us to rationalize the obtained results and to improve the stereoselectivity.

Publication Types