Asymmetric Brønsted acid catalyzed cycloadditions-efficient enantioselective synthesis of pyrazolidines, pyrazolines, and 1,3-diamines from N-acyl hyrazones and alkenes

Magnus Rueping*, Modhu Sudan Maji, Hatice Baśpínar Küçük, Iuliana Atodiresei

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

61 Scopus citations

Abstract

A general, metal-free, highly enantioselective Bronsted acid catalyzed [3+2] cycloaddition between hydrazones and alkenes has been developed that affords pyrazolidine derivatives (see scheme). The resulting optically active pyrazolidines can undergo many chemical transformations which allow, for example, the enantioselective synthesis of valuable pyrazolines and 1,3-diamines.

Original languageEnglish (US)
Pages (from-to)12864-12868
Number of pages5
JournalAngewandte Chemie - International Edition
Volume51
Issue number51
DOIs
StatePublished - Dec 14 2012

Keywords

  • heterocycles
  • homogeneous catalysis
  • hydrazones
  • hydrogen bonding
  • ion pairs

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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