The Castagnoli–Cushman Reaction

Author:

Ramiro José Luis1,Martínez-Caballero Sonia2,Neo Ana G.1ORCID,Díaz Jesús1ORCID,Marcos Carlos F.1ORCID

Affiliation:

1. Laboratory of Bioorganic Chemistry & Membrane Biophysics (L.O.B.O.), Departamento de Química Orgánica e Inorgánica, Facultad de Veterinaria, Universidad de Extremadura, 10003 Cáceres, Spain

2. Departamento de Didáctica de las Ciencias Experimentales y las Matemáticas, Facultad de Formación de Profesorado, Universidad de Extremadura, 10003 Cáceres, Spain

Abstract

Since the first reports of the reaction of imines and cyclic anhydrides by Castagnoli and Cushman, this procedure has been applied to the synthesis of a variety of lactams, some of them with important synthetic or biological interest. The scope of the reaction has been extended to the use of various Schiff bases and anhydrides as well as to different types of precursors for these reagents. In recent years, important advances have been made in understanding the mechanism of the reaction, which has historically been quite controversial. This has helped to develop reaction conditions that lead to pure diastereomers and even homochiral products. In addition, these mechanistic studies have also led to the development of new multicomponent versions of the Castagnoli–Cushman reaction that allow products with more diverse and complex molecular structures to be easily obtained.

Funder

Junta de Extremadura and ERDF

Publisher

MDPI AG

Subject

Chemistry (miscellaneous),Analytical Chemistry,Organic Chemistry,Physical and Theoretical Chemistry,Molecular Medicine,Drug Discovery,Pharmaceutical Science

Reference168 articles.

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4. Current diversity of cyclic anhydrides for the Castagnoli–Cushman-type formal cycloaddition reactions: Prospects and challenges;Krasavin;Tetrahedron Lett.,2016

5. Mal, D. (2019). Anionic Annulations in Organic Synthesis, Elsevier.

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