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

Franc Požgan, Hamad Al Mamari, Uroš Grošelj, Jurij Svete, Bogdan Stefane

Research output: Contribution to journalReview article

5 Citations (Scopus)

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.

Original languageEnglish
Article number3
JournalMolecules
Volume23
Issue number1
DOIs
Publication statusPublished - Jan 1 2018

Keywords

  • Azomethine imines
  • Metal-catalyzed cycloadditions
  • Organocatalyzed cycloadditions
  • Pyrazolidines
  • Pyrazolines
  • [3+2] cycloadditions

ASJC Scopus subject areas

  • Organic Chemistry

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