Catalytic Asymmetric Synthesis of α-Arylpyrrolidines and Benzo-fused Nitrogen Heterocycles
Catalytic Asymmetric Synthesis of α-Arylpyrrolidines and Benzo-fused Nitrogen Heterocycles
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DOI：
10.1002/anie.201814331
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发表时间：
2019-03-11
影响因子：
16.6
通讯作者：
Buchwald, Stephen L.
中科院分区：
文献类型：
--
作者：
Dai, Xi-Jie;Engl, Oliver D.;Buchwald, Stephen L.
在此，我们报告了一个实用的两步合成路线，α-芳基吡咯烷通过铃木宫浦交叉偶联和对映选择性铜催化的分子内氢胺化反应。该方法具有良好的立体选择性和广泛的底物与药学相关的杂芳烃的转化范围，使该方法成为一种实用和通用的吡咯烷合成方法。此外，这种分子内氢胺化策略促进了四氢异喹啉和中环二苯并稠合氮杂环的不对称合成。
Herein, we report a practical two-step synthetic route to alpha-arylpyrrolidines through Suzuki-Miyaura cross-coupling and enantioselective copper-catalyzed intramolecular hydroamination reactions. The excellent stereoselectivity and broad scope for the transformation of substrates with pharmaceutically relevant heteroarenes render this method a practical and versatile approach for pyrrolidine synthesis. Additionally, this intramolecular hydroamination strategy facilitates the asymmetric synthesis of tetrahydroisoquinolines and medium-ring dibenzo-fused nitrogen heterocycles.