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Asymmetric,Regioselective Bromohydroxylation of 2‐Aryl‐2‐propen‐1‐ols Catalyzed by Quinine‐Derived Catalysts
Authors:Ye Zhang  Hui Xing  Weiqing Xie  Xiaolong Wan  Yisheng Lai  Dawei Ma
Abstract: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.
Keywords:asymmetric organocatalysis  bifunctional catalysts  boron tethers  bromohydroxylation  regioselectivity
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