Tetrahedron

Stereocontrolled palladium-catalysed umpolung allylation of aldehydes with allyl acetates

M Vogt, S Ceylan, A Kirschning

Index: Vogt, Monika; Ceylan, Sascha; Kirschning, Andreas Tetrahedron, 2010 , vol. 66, # 33 p. 6450 - 6456

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Citation Number: 14

Abstract

In the present work the stereocontrolled palladium-catalysed umpolung allylation of aldehydes is described. Allyl acetates are in situ transformed into the corresponding allyl boronates, which directly react with aldehydes. The question of stereocontrol is raised by employing (a) chiral boronating agents (reagent control) and by (b) utilising chiral aldehydes (substrate control). These studies reveal that the approach based on substrate control is ...

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