Highly Chemoselective Baylis-Hillman and Aldol Reactions of 2H-Thiopyran-4(3H)-one Using Tertiary Amine Catalysts in Aqueous Media

[摘要]：For the first time the Baylis-Hillman (BH) reaction of 2H-thiopyran-4(3H)-one is investigated, and surprisingly, the reaction of 2H-thiopyran-4(3H)-one with aldehydes in the presence of different tertiary amines shows excellent chemo- and regioselectivity in water. At room temperature. DBU affords BH adducts, but with DABCO, aldol products were obtained. In the case of DABCO, Et3N, or DMAP, domino aldol-rearrangement reactions occurred at 45-50 degrees C

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