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Note | Regular issue | Vol 71, No. 5, 2007, pp.1163-1171
Published online, 27th March, 2007
DOI: 10.3987/COM-07-11022
N-Methylpseudoephedrine-Mediated Asymmetric Syntheses of O-Carboxyalkylated Flavones

Kyoung Hee Kang, Ji Hyeon Heo, Yongtae Kim, and Yong Sun Park*

*Department of Chemistry, Konkuk University, 1 Hwayangdong, Seoul 143-701, Korea

Abstract

N-Methylpseudoephedrine-mediated dynamic resolution of α-bromoacetates for stereoselective preparation of O-carboxyalkylated flavone has been developed. Substitutions with hydroxyflavone and Cs2CO3 in MeCN and following ethanolysis provided O-carboxyalkylated flavones 3-10 up to 60% overall yield and 98:2 er. In addition, we have described the regioselective alkylations of chrysin to provide 7-O-carboxyalkylated chrysins 11-13 with high enantioselectivities.