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An efficient synthetic method of N-tosyl aza-Baylis-Hillman adducts of cycloalkenones has been developed. The synthesis was carried out by FeCl3-catalyzed direct amination of the corresponding Baylis-Hillman alcohols. Compound 2a was synthesized previously by the Baylis-Hillman reaction of 2-cyclohexen-1-one and N-tosylimine. However, preparation and purification of N-tosylimine is somewhat tedious due to partial hydrolysis. Thus, our new protocol could be used efficiently as a good alternative method of this compound.
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KCS