American Chemical Society
ol101883g_si_001.pdf (1.79 MB)

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

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journal contribution
posted on 2010-10-15, 00:00 authored by Bagher Eftekhari-Sis, Ali Akbari, Klaus Harms
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 °C.