Asymmetric, Regioselective Bromohydroxylation of 2-Aryl-2-propen-1-ols Catalyzed by Quinine-Derived Catalysts

Asymmetric, Regioselective Bromohydroxylation of 2-Aryl-2-propen-1-ols Catalyzed by Quinine-Derived Catalysts
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奎宁衍生催化剂催化 2-芳基-2-丙烯-1-醇的不对称区域选择性溴羟基化

DOI:
10.1002/adsc.201200782
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发表时间:
2013-01
期刊:
Advanced Synthesis & Catalysis
影响因子:
--
通讯作者:
Ma, Dawei
Ma, Dawei
中科院分区:
其他
文献类型:
--
作者:
Xie, Weiqing;Wan, Xiaolong;Lai, Yisheng;Ma, Dawei

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研究了奎宁衍生双功能催化剂催化2-芳基-2-丙烯-1-醇的不对称溴羟基化反应。通过使用原位形成的硼酸酯作为系链来控制区域选择性,并利用奎宁衍生的双功能催化剂同时活化硼酸酯和N-溴代琥珀酰亚胺(NBS)来引入对映体选择性。手性溴代醇是有机合成中的有用原料,在两步反应序列中以中等至优异的对映选择性制备。
The asymmetric bromohydroxylation of 2‐aryl‐2‐propen‐1‐ols catalyzed by quinine‐derived bifunctional catalyst has been developed. The regioselectivity was controlled by employing a boronate ester as tether which was formed in situ and enantioselectivity was introduced by taking advantage of a quinine‐derived bifunctional catalyst which activated the boronate ester and N‐bromosuccinimide (NBS) at the same time. Chiral bromohydrin, which is a useful feedstock in organic synthesis, was produced in moderate to excellent enantioselectivity in a two‐step reaction sequence.
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