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

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

Abstract

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.

Keywords

pirazolini;pirazolidini;kovinsko katalizirane cikloadicije;organokatalizirane cikloadicije;azometin imini;[3+2] cikloadicije;pyrazolines;pyrazolidines;metal-catalyzed cycloadditions;organocatalyzed cycloadditions;azomethine imines;[3+2] cycloadditions;

Data

Language:	English
Year of publishing:	2018
Typology:	1.02 - Review Article
Organization:	UL FKKT - Faculty of Chemistry and Chemical Technology
UDC:	547.77
COBISS:	1537674179
ISSN:	1420-3049
Views:	191
Downloads:	67
Average score:	0 (0 votes)
Metadata:

Other data

Secondary language:	Slovenian
Secondary keywords:	pirazolini;pirazolidini;kovinsko katalizirane cikloadicije;organokatalizirane cikloadicije;azometin imini;[3+2] cikloadicije;
Type (COBISS):	Article
Pages:	str. 1-31
Volume:	ǂVol. ǂ23
Issue:	ǂiss. ǂ1
Chronology:	2018
DOI:	10.3390/molecules23010003
ID:	13646708