Synthesis of Diastereoenriched α-Aminomethyl Enaminones via a Brønsted Acid-Catalyzed Asymmetric aza-Baylis-Hillman Reaction of Chiral N-Phosphonyl Imines

Yangxue Liu, Sultan Ahmed, Xiao Yan Qin, Hossein Rouh, Guanzhao Wu, Guigen Li, Bo Jiang

Research output: Contribution to journalArticlepeer-review

3 Scopus citations

Abstract

An effective chiral GAP methodology for preparing α-aminomethyl enaminones through a (R)-CSA-catalyzed asymmetric aza-Baylis-Hillman reaction is reported. Excellent yields and high diastereoselectivity could be obtained under mild conditions and convenient GAP techniques. The confirmations of the absolute configuration of N-phosphonyl imine and chiral enaminone by X-ray diffraction provides an explicit explanation of the chirality mechanism for GAP chemistry.

Original languageEnglish
Pages (from-to)1125-1131
Number of pages7
JournalChemistry - An Asian Journal
Volume15
Issue number7
DOIs
StatePublished - Apr 1 2020

Keywords

  • Asymmetric synthesis
  • Aza-Baylis-Hillman reaction
  • Brønsted Acid Catalysis
  • GAP chemistry
  • α-Aminomethyl enaminones

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