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The drawback to this methodology is its slow reaction rate, and many research groups have examined a variety of methods to accelerate the reaction. Among the activated alkenes cycloalkenones are famous. 1b Under the normal reaction conditions using DABCO (1,4-diazabicyclo[2.2.2]octane) no reaction was observed. Recently, various methods for the synthesis of the BaylisHillman adducts of cycloalkenones have been developed with certain limitations. (1) The combination of 2,6-diphenyl-4H-chalcogenopyran-4-ones (or -4-thions) and TiCl 4 in methylene chloride 2a and related methods were developed for the reactive p-nitrobenzaldehyde and 2-cyclohexen-1one or 2-cyclopenten-1-one. 2 (2) The combination of lithium perchlorate (LiClO4) and DABCO in ether could be used for the Baylis-Hillman reaction of benzaldehyde and 2-cyclohexen-1-one. 3 (3) The use of Et 2AlI in CH2Cl2 for the reaction of enone isolevoglucosenone and Cβ-D-galactopyranosylformaldehyde furnished the corresponding BaylisHillman adduct. 4 (4) 4-(Dimethylamino)pyridine (DMAP)catalyzed hydroxymethylation of 2-cyclohexenones with formaldehyde was carried out effectively in aqueous medium. 5

The Most Simple and Convenient Synthesis of the Baylis-Hillman Adducts of Cycloalkenones:Use of DMAP in Aqueous THF