Trillo P, Baeza A, * Nájera C. * Universidad de Alicante, Spain
Copper-Catalyzed Asymmetric Alkylation of β-Keto Esters with Xanthydrols.
Adv. Synth. Catal. 2013;
355: 2815-2821
Key words
asymmetric alkylation - β-keto esters - copper
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.
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.
