Synfacts 2008(4): 0399-0399  
DOI: 10.1055/s-2008-1042796
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Indium-Catalyzed Enantioselective Allylation of α-Keto Phosphonates

Contributor(s): Mark Lautens, Praew Thansandote
J. Huang, J. Wang, X. Chen, Y. Wen, X. Liu, X. Feng*
Sichuan University, Chengdu, P. R. of China
Further Information

Publication History

Publication Date:
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.