Catalytic, asymmetric, "interrupted" Feist-Benary reactions
Catalytic, asymmetric, "interrupted" Feist-Benary reactions
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DOI：
10.1021/ja055752d
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发表时间：
2005-10-26
影响因子：
15
通讯作者：
Flaschenriem, C
中科院分区：
文献类型：
--
作者：
Calter, MA;Phillips, RM;Flaschenriem, C
金鸡纳生物碱的嘧啶衍生物是“中断”的Feist−Bénary反应的优良不对称催化剂。该反应以简单的原料为原料，在温和的条件下合成高取代度的羟基二氢呋喃。不对称反应对未取代的溴代酮有较高的对映选择性，对取代底物有较高的对映和非对映选择性。机理实验表明，生物碱衍生物的氢溴酸盐是反应的活性催化剂。
Pyrimidine derivatives of the cinchona alkaloids function as excellent asymmetric catalysts for the “Interrupted” Feist−Bénary Reaction. This reaction produces highly substituted hydroxydihydrofurans from simple starting materials under mild conditions. The asymmetric reaction gives high enantioselectivities with unsubstituted bromoketones, and high enantio- and diastereoselectivities with substituted substrates. Mechanistic experiments suggest that the hydrobromide salt of the alkaloid derivative is the active catalyst for the reaction.