Synthesis 2017; 49(07): 1509-1518
DOI: 10.1055/s-0036-1588725
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© Georg Thieme Verlag Stuttgart · New York

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

Sara Meninno
a  Dipartimento di Chimica e Biologia ‘A. Zambelli’, Università di Salerno, Via Giovanni Paolo II, 84084 Fisciano, Italy   Email: lattanzi@unisa.it
,
Jacob Overgaard
b  Department of Chemistry, Aarhus University, Langelandsgade 140, 8000 Aarhus, Denmark
,
Alessandra Lattanzi*
a  Dipartimento di Chimica e Biologia ‘A. Zambelli’, Università di Salerno, Via Giovanni Paolo II, 84084 Fisciano, Italy   Email: lattanzi@unisa.it
› Author Affiliations
Further Information

Publication History

Received: 28 December 2016

Accepted after revision: 27 January 2017

Publication Date:
21 February 2017 (online)


Dedicated to Professor Arrigo Scettri on the occasion of his 70th birthday

Abstract

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.

Supporting Information

 
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