Download PDF
Synfacts 2014; 10(1): 0044
DOI: 10.1055/s-0033-1340437
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Alkylation of β-Keto Esters

Contributor(s):
Hisashi Yamamoto
,
Sukalyan Bhadra
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
CrossrefGoogle Scholar
Further Information

Publication History

Publication Date:
13 December 2013 (online)

 
 PDF Download Permissions and Reprints

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.


#
#


   Permissions and Reprints