Mixed organofluorine-organosilicon chemistry. 13. One-pot synthesis of difluoroaldols from acylsilanes and trifluoromethyltrimethylsilane. Application to the synthesis of a difluoro analogue of egomaketone
Mixed organofluorine-organosilicon chemistry. 13. One-pot synthesis of difluoroaldols from acylsilanes and trifluoromethyltrimethylsilane. Application to the synthesis of a difluoro analogue of egomaketone
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DOI：
10.1021/jo001549j
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发表时间：
2001-03-23
影响因子：
3.6
通讯作者：
Portella, C
中科院分区：
文献类型：
--
作者：
Lefebvre, O;Brigaud, T;Portella, C
以酰基硅烷1、三氟甲基三甲基硅烷（TFMTMS）和醛为原料，采用一锅法合成了二氟羟醛化合物3。该反应的关键中间体是二氟烯氧基硅烷2。三氟甲磺酸镱被证明是一个非常有效的催化剂，促进羟醛型反应在非常温和的条件下。通过相应的羟醛化合物3d脱水合成二氟异丁酮7d，说明了该反应用于收敛合成二氟化合物的潜力。
Difluoroaldol compounds 3 were synthesized in a one-pot procedure involving an acylsilane 1, trifluoromethyltrimethylsilane (TFMTMS), and an aldehyde. The key intermediate of this reaction is a difluoroenoxysilane 2. Ytterbium triflate proved to be a very efficient catalyst for promoting the aldol type reaction under very mild conditions. The potential of this reaction for the convergent synthesis of difluorinated compounds was illustrated by the synthesis of difluoroegomaketone 7d through dehydration of the corresponding aldol compound 3d.