Organocatalytic Michael Reaction of Nitroenamine Derivatives with Aldehydes: Short and Efficient Asymmetric Synthesis of (-)-Oseltamivir

Jiang Weng, Yong Bo Li, Rui Bin Wang, Gui Lu*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

34 Scopus citations

Abstract

Nitroenamine derivatives were used as a new class of Michael acceptors in the organocatalytic Michael reaction of aldehydes. The addition products were obtained in good yields and very good to excellent enantioselectivities. Moreover, a highly efficient, enantioselective, and simple synthesis of (-)-oseltamivir was accomplished in only five steps: two separate one-pot operations and one purification step. This procedural simplicity demonstrated the power of the organocatalytic asymmetric Michael reaction of nitroenamine acceptors with aldehydes.

Original languageEnglish
Pages (from-to)1007-1012
Number of pages6
JournalChemCatChem
Volume4
Issue number7
DOIs
StatePublished - Jul 2012
Externally publishedYes

Keywords

  • Asymmetric synthesis
  • Michael addition
  • Nitroenamines
  • Organocatalysis
  • Oseltamivir

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