Synthesis of non-racemic pyrazolines and pyrazolidines by [3+2] cycloadditions of azomethine imines

Požgan, Franc (author), Al Mamari, Hamad (author), Grošelj, Uroš (author), Svete, Jurij (author), Štefane, Bogdan (author)

Asymmetric [3+2] cycloadditions of azomethine imines comprise a useful synthetic tool for the construction of pyrazole derivatives with a variable degree of saturation and up to three stereogenic centers. As analogues of pyrrolidines and imidazolidines that are abundant among natural products, pyrazoline and pyrazolidine derivatives represent attractive synthetic targets due to their extensive applications in the chemical and medicinal industries. Following the increased understanding of the mechanistic aspect of metal-catalyzed and organocatalyzed [3+2] cycloadditions of 1,3-dipoles gained over recent years, significant strides have been taken to design and develop new protocols that proceed efficiently under mild synthetic conditions and duly benefit from superior functional group tolerance and selectivity. In this review, we represent the current state of the art in this field and detailed methods for the synthesis of non-racemic pyrazolines and pyrazolidines via [3+2] metal and organocatalyzed transformations reported since the seminal work of Kobayashi et al. and Fu et al. in 2002 and 2003 up to the end of year 2017.

• Language: English
• Keywords: pyrazolines, pyrazolidines, metal-catalyzed cycloadditions, organocatalyzed cycloadditions, azomethine imines, [3+2] cycloadditions
• Work type: Article
• Typology: 1.02 - Review Article
• Organization: FKKT - Faculty of Chemistry and Chemical Technology
• Publication status: Published
• Publication version: Version of Record
• Year: 2018
• Number of pages: 31 str.
• Numbering: Vol. 23, iss. 1, art. 3
• PID: 20.500.12556/RUL-131880
• UDC: 547.77
• ISSN on article: 1420-3049
• DOI: 10.3390/molecules23010003
• COBISS.SI-ID: 1537674179
• Publication date in RUL: 05.10.2021

Record is a part of a journal

• Title: Molecules
• Shortened title: Molecules
• Publisher: MDPI
• ISSN: 1420-3049
• COBISS.SI-ID: 18462981

Licences

• License: CC BY 4.0, Creative Commons Attribution 4.0 International
• Link: http://creativecommons.org/licenses/by/4.0/
• Description: This is the standard Creative Commons license that gives others maximum freedom to do what they want with the work as long as they credit the author.
• Licensing start date: 01.01.2018

Secondary language

• Language: Slovenian
• Keywords: pirazolini, pirazolidini, kovinsko katalizirane cikloadicije, organokatalizirane cikloadicije, azometin imini, [3+2] cikloadicije

Projects

• Funder: ARRS - Slovenian Research Agency
• Project number: P1-0179
• Name: Sinteze in transformacije organskih spojin. Novi reagenti v stereoselektivni in regioselektivni sintezi aminokislin kot intermediatov v organski sintezi