2H-噻喃-4(3H)-酮在水相介质中用叔胺催化剂的高化学选择性 Baylis-Hillman 和 aldol 反应。
Highly chemoselective Baylis-Hillman and aldol reactions of 2H-thiopyran-4(3H)-one using tertiary amine catalysts in aqueous media.
机构信息
Department of Chemistry, Faculty of Science, University of Maragheh, Golshar, P.O. Box. 55181-83111, Maragheh, Iran.
出版信息
Org Lett. 2010 Oct 15;12(20):4568-71. doi: 10.1021/ol101883g.
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.
首次研究了 2H-噻喃-4(3H)-酮的 Baylis-Hillman（BH）反应，令人惊讶的是，在水相中，2H-噻喃-4(3H)-酮与不同叔胺存在的醛反应表现出极好的化学和区域选择性。在室温下，DBU 提供 BH 加合物，但使用 DABCO 时，则得到 aldol 产物。在 DABCO、Et(3)N 或 DMAP 的情况下，在 45-50°C 下发生了串联 aldol-重排反应。
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