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Indium-Catalyzed Enantioselective Allylation of α-Keto Phosphonates
J. Huang, J. Wang, X. Chen, Y. Wen, X. Liu, X. Feng*
Sichuan University, Chengdu, P. R. of China
19 March 2008 (online)
The first enantioselective allylation of aromatic α-keto phosphonates is described using an indium(III) catalyst and a chiral (S)-ramipril acid derived ligand. Good to excellent yields and enantioselectivities are seen for a variety of aromatic phosphonates. The yields and/or ee values are sensitive to steric hindrance in the ester and aromatic moieties of the aromatic phosphonates. For example, ee values decreased from the methyl to the larger isopropyl ester and from the phenyl to the ortho-substituted aromatic compounds.