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Molecules 2018, 23(1), 3; doi:10.3390/molecules23010003

Synthesis of Non-Racemic Pyrazolines and Pyrazolidines by [3+2] Cycloadditions of Azomethine Imines

1
Faculty of Chemistry and Chemical Technology, University of Ljubljana, Večna pot 113, SI 1000 Ljubljana, Slovenia
2
Department of Chemistry, College of Science, Sultan Qaboos University, P.O. Box 36, Al Khoud Muscat, Oman
*
Author to whom correspondence should be addressed.
Received: 29 November 2017 / Revised: 12 December 2017 / Accepted: 12 December 2017 / Published: 21 December 2017
(This article belongs to the Special Issue Pyrazole Derivatives)

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. View Full-Text
Keywords: pyrazolines; pyrazolidines; metal-catalyzed cycloadditions; organocatalyzed cycloadditions; azomethine imines; [3+2] cycloadditions pyrazolines; pyrazolidines; metal-catalyzed cycloadditions; organocatalyzed cycloadditions; azomethine imines; [3+2] cycloadditions
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Požgan, F.; Al Mamari, H.; Grošelj, U.; Svete, J.; Štefane, B. Synthesis of Non-Racemic Pyrazolines and Pyrazolidines by [3+2] Cycloadditions of Azomethine Imines. Molecules 2018, 23, 3.

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