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Communication | Regular issue | Vol 71, No. 1, 2007, pp.5-11
Published online, 24th November, 2006
DOI: 10.3987/COM-06-10910
Diacetone-D-glucose-Mediated Asymmetric Syntheses of Dihydroquinoxalinones

Yongtae Kim, Min Hee Lee, Eui Ta Choi, Eun Sun No, and Yong Sun Park*

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

Abstract

Asymmetric syntheses of dihydroquinoxalinones by diacetone-D-glucose mediated nucleophilic substitution of α-bromo esters have been investigated. Stereoselective reactions with various 1,2-phenylenediamine nucleophiles in the presence of TBAI and DIEA and following spontaneous removal of the chiral auxiliary can provide dihydroquinoxalinones (3-9) up to 92% yield and 97:3 er. In addition, we have described the regio- and stereoselective reactions of non-symmetric 1,2-phenylenediamine nucleophiles to provide 10-14 up to 90:10 regioisomeric ratio and 98:2 er.