Pd(OAc)_2-Catalyzed Isomerization of Acetates of the Baylis-Hillman Adducts

摘要

Since the pioneering work of Baylis and Hillman the 1,4-diazabicyclo[2,2,2]octane(DABCO)-catalyzed coupling of aldehydes with activated alkenes to give allylic alcohols is largely employed and continues to stimulate research due to its immense synthetic potential.Among them,stereoselective isomerization of acetates of the Baylis-Hillman adducts catalyzed by trimethylsilyl trifluoromethanesulfonate,tri-fluoroacetic acid,benzyltrimethylammonium fluoride,DABCO and montmorillonite K10 clay has appeared in the literature.As a part of our research program aimed at the development of the Baylis-Hillman reaction,particularly for the construction of heterocycles,we decided to investigate the Pd(OAc)_2-catalyzed stereoselective isomerization of the acetates of the Baylis-Hillman adducts.