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Synfacts 2014; 10(1): 0044
DOI: 10.1055/s-0033-1340437
DOI: 10.1055/s-0033-1340437
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
Enantioselective Alkylation of β-Keto Esters
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
13. Dezember 2013 (online)
Significance
The Cu(OTf)2/tert-butyl-bis-oxazoline catalyst system allows the asymmetric alkylation of β-keto esters with free benzylic alcohols, for example, xanthydrols as alkylating agents. The reaction is environmentally benign as it generates only water as by-product.
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Comment
The reaction between the asymmetric Cu(II)-β-keto ester derivative and the in situ generated carbocation proceeds via an SN1 mechanism. Albeit unknown, the water produced has a specific role to facilitate the reaction.
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