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

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

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.

• Jezik: Angleški jezik
• Ključne besede: pyrazolines, pyrazolidines, metal-catalyzed cycloadditions, organocatalyzed cycloadditions, azomethine imines, [3+2] cycloadditions
• Vrsta gradiva: Članek v reviji
• Tipologija: 1.02 - Pregledni znanstveni članek
• Organizacija: FKKT - Fakulteta za kemijo in kemijsko tehnologijo
• Status publikacije: Objavljeno
• Različica publikacije: Objavljena publikacija
• Leto izida: 2018
• Št. strani: 31 str.
• Številčenje: Vol. 23, iss. 1, art. 3
• PID: 20.500.12556/RUL-131880
• UDK: 547.77
• ISSN pri članku: 1420-3049
• DOI: 10.3390/molecules23010003
• COBISS.SI-ID: 1537674179
• Datum objave v RUL: 05.10.2021

Gradivo je del revije

• Naslov: Molecules
• Skrajšan naslov: Molecules
• Založnik: MDPI
• ISSN: 1420-3049
• COBISS.SI-ID: 18462981

Licence

• Licenca: CC BY 4.0, Creative Commons Priznanje avtorstva 4.0 Mednarodna
• Povezava: http://creativecommons.org/licenses/by/4.0/deed.sl
• Opis: To je standardna licenca Creative Commons, ki daje uporabnikom največ možnosti za nadaljnjo uporabo dela, pri čemer morajo navesti avtorja.
• Začetek licenciranja: 01.01.2018

Sekundarni jezik

• Jezik: Slovenski jezik
• Ključne besede: pirazolini, pirazolidini, kovinsko katalizirane cikloadicije, organokatalizirane cikloadicije, azometin imini, [3+2] cikloadicije

Projekti

• Financer: ARRS - Agencija za raziskovalno dejavnost Republike Slovenije
• Številka projekta: P1-0179
• Naslov: Sinteze in transformacije organskih spojin. Novi reagenti v stereoselektivni in regioselektivni sintezi aminokislin kot intermediatov v organski sintezi