MICHAEL-ADDITION REACTIONS OF LEVOGLUCOSENONE

Article abstract of DOI:10.1016/S0008-6215(00)88064-7

The Michael-addition reactions of levoglucosenone with diethyl malonate, ethyl cyanoacetate, 2-nitropropane, and 2-methylcyclohexanone have been examined, using a variety of catalysts.This reaction may be conveniently used to prepare, in reasonable yields, 4-substituted levoglucosenone derivatives having the D-erythro configuration.Better yields of the diethyl malonate adduct were obtained on using bis(2,4-pentanedionate)-Ni(II) as the catalyst.