Tetrahedron

Palladium-catalysed Heck reaction on 1, 2-dien-1-ols: a stereoselective synthesis of α-arylated α, β-unsaturated aldehydes

A Deagostino, C Prandi, A Toppino, P Venturello

Index: Deagostino, Annamaria; Prandi, Cristina; Toppino, Antonio; Venturello, Paolo Tetrahedron, 2008 , vol. 64, # 45 p. 10344 - 10349

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Citation Number: 10

Abstract

A new methodology for preparing α-arylated α, β-unsaturated aldehydes is reported. The starting materials are all commercially available alkyn-1-ols (1a–c) that have been easily isomerised to the corresponding allenes (2a–c). The key step is the Heck coupling of the 1, 2- dien-1-ols with a series of iodo-and bromoarene. The products have been synthesised in good yields, and the reactions were carried out under very mild conditions.