Enantioselective protonation of itaconimides with thiols and the rotational kinetics of the axially chiral C-N bond

Shishi Lin*, Dasheng Leow, Kuo-Wei Huang, Choon Hong Tan

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

40 Scopus citations

Abstract

Bicyclic guanidines are able to catalyze the protonation reactions of 2- phthalimidoacrylates with thiols in excellent yields and enantioselectivities. The protonation reaction of itaconimides with secondary phosphine oxides is also known. Herein, the tandem conjugate addition-enantioselective protonation of Nsubstituted itaconimides with thiols catalyzed by chiral bicyclic guanidine is investigated. The rotational barrier of the C-N axis of N-2-tert-butyl phenylitaconimide is also studied, both experimentally and computationally.

Original languageEnglish (US)
Pages (from-to)1741-1744
Number of pages4
JournalChemistry - An Asian Journal
Volume4
Issue number11
DOIs
StatePublished - Nov 2 2009

Keywords

  • Asymmetric catalysis
  • Atropisomerism
  • Guanidines
  • Organocatalysis
  • Protonation

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry

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