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

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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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Document Type: Communications

Affiliations: 1: State Key Laboratory of Natural Medicines, Center of Drug Discovery, China Pharmaceutical University, Nanjing 210009, People's Republic of China, phone: (+86)-25-8327-1015, Fax: (+86)-25-8327-1015 2: State Key Laboratory of Bioorganic & Natural Products Chemistry, Shanghai Institute of Organic Chemistry Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, Peole's Republic of China, phone: (+86)-21-5492-5341, Fax: (+86)-21-6416-6128

Publication date: 2013-01-14

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