Lewis base activation of Lewis acids: Catalytic enantioselective glycolate aldol reactions
Lewis base activation of Lewis acids: Catalytic enantioselective glycolate aldol reactions
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DOI：
10.1002/anie.200705499
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发表时间：
2008-01-01
影响因子：
16.6
通讯作者：
Chung, Won-Jin
中科院分区：
文献类型：
--
作者：
Denmark, Scott E.;Chung, Won-Jin
在SiCl 4和手性双磷酰胺催化剂存在下，由适当取代的羟基乙酸酯衍生的甲硅烷基烯酮缩醛可以高的非对映选择性和对映选择性得到顺式和反式1，2-二醇（见反应路线; TMS=三甲基甲硅烷基，TBS=叔丁基二甲基甲硅烷基）。非对映选择性的意义可以通过改变甲硅烷基烯酮缩醛上取代基的大小来逆转。
(Chemical Equation Presented) Both syn-and anti-1, 2-diols can be obtained with high diastereoselectivity and enantioselectivity from the properly substituted glycolate-derived silyl ketene acetals in the presence of SiCl 4 and a chiral bisphosphoramide catalyst (see scheme; TMS= trimethylsilyl, TBS= tert-butyldimethylsilyl). The sense of diastereoselectivity can be reversed by changing the size of the substituents on the silyl ketene acetals.