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, Et(3)N, or DMAP, domino aldol-rearrangement reactions occurred at 45-50 °C.
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| http://dx.doi.org/10.1021/ol101883g | DOI Listing |
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