Cu-Fe Spinels: First Heterogeneous and Magnetically Recoverable Catalyst for the Ferrier Rearrangement of 2-Nitroglycals-Reference-Cited by-同舟云学术

Cu-Fe Spinels: First Heterogeneous and Magnetically Recoverable Catalyst for the Ferrier Rearrangement of 2-Nitroglycals

Published:2019-04-23 Issue:6 Volume:16 Page:447-453
ISSN:1570-1786
Container-title:Letters in Organic Chemistry
language:en
Short-container-title:LOC

Author:

Lafuente Leticia¹,Rochetti María Florencia²,Bravo Rodolfo¹,Sasiambarrena Leandro¹,Santiago Cintia C.¹,Ponzinibbio Agustín¹

Affiliation:

1. Centro de Estudio de Compuestos Organicos (CEDECOR), Departamento de Quimica, Facultad de Ciencias Exactas, Universidad Nacional de La Plata, 47 y 115, 1900, La Plata, Argentina

2. Centro de Investigacion y Desarrollo en Ciencias Aplicadas , Argentina

Abstract

Cu-Fe spinels promoted the Ferrier rearrangement of 2-nitroglycals with several O-nucleophiles. 2,3-Unsaturated carbohydrate derivatives were prepared by the reaction of 3,4,6-tri-Oacetyl- 2-nitroglucal and alcohols in the presence of 5 % of CuFe2O4. After separation of the catalyst with an external magnet, the reaction products were obtained in good yields and high stereo and regioselectivity. Also, S- and heterocyclic C-3 substituted 2-nitro-endo-glycals could be prepared by this method.

Publisher

Bentham Science Publishers Ltd.

Subject

Organic Chemistry,Biochemistry

Reference18 articles.

1. Delaunay T, Poisson T, Jubault P, Pannecoucke X. Eur J Org Chem, , 2014, 34, 7525-7546,

2. Pachamuthu K, Schmidt RR. Synlett, , 2003, 9, 1355-1357,

3. Khodair AI, Pachamuthu K, Schmidt RR. Synthesis, , 2004, 1, 53-58,

4. Khodair AI, Schmidt RR. Eur J Org Chem, , 2011, 36, 7407-7413,

5. Zhang Q, Sun J, Zhang F, Yu B. Eur J Org Chem, , 2010, 19, 3579-3582,

Cited by 11 articles. 订阅此论文施引文献订阅此论文施引文献，注册后可以免费订阅5篇论文的施引文献，订阅后可以查看论文全部施引文献

1. Recent Advances of 2‐Nitroglycals as Powerful Glycosyl Donors;European Journal of Organic Chemistry;2024-03-20

2. Controllable 1,3-Bis-Functionalization of 2-Nitroglycals with High Regioselectivity and Stereoselectivity Enabled by a H-Bond Catalyst;JACS Au;2024-03-11

3. Synthesis of 2-Nitro-2,3-Unsaturated Glycosides by a Nanomagnetic Catalyst Fe3O4@C@Fe(III);Frontiers in Chemistry;2022-05-11

4. Citric acid mediated simple and stereoselective synthesis of o-linked glycosides by Ferrier rearrangement;Results in Chemistry;2022-01

5. New insights into the reactivity of 2-halo-glycals: Synthesis of novel iodinated O- and S-glycosides;Tetrahedron Letters;2021-11