N-carbamate protected amino acid derived guanidine organocatalysts

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  • Zahraa S. Al-Taie
    Al-Nahrain University, Baghdad
  • Joseph M. Anderson
    Bangor University
  • Laura Bischoff
    Bangor University
  • Jeppe Christensen
    Diamond Light Source, Didcot
  • Simon J. Coles
    University of Southampton
  • Richard Froom
  • Mari E. Gibbard
    Bangor University
  • Leigh F. Jones
    University of Wolverhampton
  • Frank F. J. de Kleijne
    Bangor University
  • Paddy Murphy
  • Emma Thompson
    Bangor University
We report the preparation of a range of N-protected amino acid derived guanidine organocatalysts and their application to the Michael addition of 2-hydroxy-1,4-napthoquinone to β-nitrostyrene, achieving a maximum ee of 26%. Whilst these catalysts gave poor ees, the structural variation together with the X-ray crystallographic study of the intra- and intermolecular hydrogen bonding reported suggest that the C2-symmetric catalysts are lead compounds for the further development of this methodology.

Keywords

  • Amino acids, Guanidines, H-bonded extended networks, Organocatalysis
Original languageEnglish
Article number132093
JournalTetrahedron
Volume89
Early online date2 Apr 2021
DOIs
Publication statusPublished - 4 Jun 2021

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