Tetrahedron

Assessing the scope of the tandem Michael/intramolecular aldol reaction mediated by secondary amines, thiols and phosphines

…, S Fratucello, PM Brown, T Gelbrich, MB Hursthouse

Index: Richards, Elinor L; Murphy, Patrick J; Dinon, Francesca; Fratucello, Silvia; Brown, Paul M; Gelbrich, Thomas; Hursthouse, Michael B Tetrahedron, 2001 , vol. 57, # 36 p. 7771 - 7784

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Citation Number: 62

Abstract

The outcome of a tandem Michael/intramolecular aldol reaction which is mediated by secondary amines, thiols and phosphines has been found to be highly substrate dependent, with the best results being obtained for the formation of 5 and 6-membered rings using thiol or thiolate nucleophiles. Amine and phosphine mediated cyclisations were found to be problematic in several cases but were still effective methods for the formation of 5–7 ...