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Straightforward Synthesis of Allylated Keto Esters: The Palladium‐Catalysed Haloketone Alkoxycarbonylation/ Allylation Domino Reaction
Author(s) -
Wahl Benoit,
Giboulot Steven,
Mortreux André,
Castanet Yves,
Sauthier Mathieu,
Liron Frédéric,
Poli Giovanni
Publication year - 2012
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201100848
Subject(s) - chemistry , xantphos , palladium , nucleophile , domino , tsuji–trost reaction , allylic rearrangement , ketone , catalysis , carbonylation , ligand (biochemistry) , organic chemistry , alkylation , combinatorial chemistry , carbon monoxide , biochemistry , receptor
The palladium‐catalysed α‐chloro ketone methoxycarbonylation and allylic alkylation reactions can be efficiently combined to provide a new catalytic domino reaction. The first, carbonylative, step generates the β‐keto ester, which acts as the nucleophile in a subsequent allylation step. The use of allyl phenates in combination with Xantphos ligand are the key features allowing one to obtain the allylated β‐keto esters in good yields