Preparation of indole-phosphine oxazoline (IndPHOX) ligands and their application in allylic alkylation

Two classes of indole-phosphine oxazoline ligands have been prepared from readily available starting materials in good overall yields. These modular ligands include an indole skeleton with either a phosphine moiety or an oxazoline ring at the 2- or 3-position, respectively. The utility of these liga...

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Bibliographic Details
Published in:Tetrahedron: asymmetry 2010-10, Vol.21 (19), p.2376-2384
Main Authors: Wang, Yu, Hämäläinen, Antti, Tois, Jan, Franzén, Robert
Format: Article
Language:English
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Summary:Two classes of indole-phosphine oxazoline ligands have been prepared from readily available starting materials in good overall yields. These modular ligands include an indole skeleton with either a phosphine moiety or an oxazoline ring at the 2- or 3-position, respectively. The utility of these ligands was demonstrated in a catalytic asymmetric reaction: the palladium-catalyzed allylic alkylation of 1,3-diphenyl-2-propenyl acetate with dimethyl malonate was performed with enantioselectivities as high as 98%.
ISSN:0957-4166
1362-511X
DOI:10.1016/j.tetasy.2010.08.008