Usuda Hiroyuki, Kuramochi Akiyoshi, Kanai Motomu, Shibasaki Masakatsu
Graduate School of Pharmaceutical Sciences, The University of Tokyo, Tokyo 113-0033, Japan.
Org Lett. 2004 Nov 11;6(23):4387-90. doi: 10.1021/ol048018s.
A new method for the catalytic enantioselective Diels-Alder reaction using polysubstituted silyl enol ethers as dienes is described. High enantioselectivity (up to 92% ee) was produced using a catalyst generated from FeBr(3) and AgSbF(6) in a 1:2 ratio and aryl-pybox (aryl = Ph or p-ethoxyphenyl). This reaction should facilitate the enantioselective synthesis of polycyclic acylphloroglucinols such as hyperforin or garsubellin A, which are currently of interest from synthetic and medicinal points of view.
本文描述了一种使用多取代甲硅烷基烯醇醚作为双烯体进行催化对映选择性狄尔斯-阿尔德反应的新方法。使用由FeBr(3)和AgSbF(6)以1:2比例以及芳基-吡唑啉酮（芳基 = 苯基或对乙氧基苯基）生成的催化剂，可实现高达92% ee的高对映选择性。该反应应有助于对映选择性合成多环酰基间苯三酚，如贯叶连翘素或加苏贝林A，从合成和药用角度来看，这些化合物目前备受关注。
