Organocatalytic one-pot asymmetric synthesis of functionalized spiropyrazolones

Via a Michael-aldol sequential reaction

Mamatha Amireddy, Kwunmin Chen

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

An efficient organocatalytic method was developed for synthesizing functionalized spiropyrazolone derivatives containing four contiguous stereogenic centres by using a Michael-aldol consecutive reaction. We applied a quinine-derived squaramide catalyst to catalyze a reaction between 3-methyl-1-aryl-2-pyrazolin-5-ones and (E)-5-nitro-6-aryl-hex-5-en-2-ones, realizing the desired spiropyrazolones in moderate-to-good yields (up to 80%) with good-to-excellent stereoselectivities (up to >20:1 dr, 94% ee).

Original languageEnglish
Pages (from-to)77474-77480
Number of pages7
JournalRSC Advances
Volume6
Issue number81
DOIs
Publication statusPublished - 2016 Jan 1

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Pyrazolones
Stereoselectivity
Quinine
Derivatives
Catalysts
3-hydroxybutanal

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)

Cite this

Organocatalytic one-pot asymmetric synthesis of functionalized spiropyrazolones : Via a Michael-aldol sequential reaction. / Amireddy, Mamatha; Chen, Kwunmin.

In: RSC Advances, Vol. 6, No. 81, 01.01.2016, p. 77474-77480.

Research output: Contribution to journalArticle

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