Catalytic asymmetric construction of spiro(γ-butyrolactam-γ- butyrolactone) moieties through sequential reactions of cyclic imino esters with Morita-Baylis-Hillman bromides

Huai Long Teng, He Huang, Chun Jiang Wang*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

44 Citations (Scopus)

Abstract

Spiro(γ-butyrolactam-γ-butyrolactone): A route to enantioenriched spiro(γ-butyrolactam-γ-butyrolactone) compounds, a valuable motif for drug discovery, was developed by use of a highly efficient copper(I)/TF-BiphamPhos-catalyzed tandem Michael addition-elimination of homoserine lactone derived cyclic imino esters with Morita-Baylis-Hillman (MBH) bromides, followed by treatment with para-toluenesulfonic acid (see scheme).

Original languageEnglish
Pages (from-to)12614-12618
Number of pages5
JournalChemistry - A European Journal
Volume18
Issue number40
DOIs
Publication statusPublished - 1 Oct 2012
Externally publishedYes

Keywords

  • asymmetric catalysis
  • bromides
  • diastereoselectivity
  • enantioselectivity
  • imino esters
  • spiro compounds

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Teng, H. L., Huang, H., & Wang, C. J. (2012). Catalytic asymmetric construction of spiro(γ-butyrolactam-γ- butyrolactone) moieties through sequential reactions of cyclic imino esters with Morita-Baylis-Hillman bromides. Chemistry - A European Journal, 18(40), 12614-12618. https://doi.org/10.1002/chem.201201475