Amine Thiourea Catalysed Double Michael Reaction: An Approach for the Asymmetric Synthesis of Spiro[pyrazolone-4,3′-tetrahydrothiophenes]

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  • Sara Meninno, University of Salerno
  • ,
  • Jacob Overgaard
  • Alessandra Lattanzi, University of Salerno

A domino reaction, based on an organocatalysed sulfa-Michael­/Michael sequence, is demonstrated as being useful for the asymmetric synthesis of spiro[pyrazolone-4,3′-tetrahydrothiophenes] bearing three consecutive stereocentres. This new class of spirocyclic compounds has been synthesised in good yield and fairly good diastereo- and enantioselectivity by reacting α,β-unsaturated pyrazolones and tert-butyl (E)-4-mercapto-2-butenoate in the presence of a readily available secondary amine thiourea derived from (R,R)-1,2-diphenylethylenediamine.

OriginalsprogEngelsk
TidsskriftSynthesis
Vol/bind49
Nummer7
Sider (fra-til)1509-1518
Antal sider10
ISSN0039-7881
DOI
StatusUdgivet - 2017

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