Zheng Purui, Han Xiaoyu, Hu Jiao, Zhao Xiaoming, Xu Tao
Shanghai Key Laboratory of Chemical Assessment and Sustainability, School of Chemical Science and Engineering , Tongji University , 1239 Siping Road , Shanghai , 200092 , People's Republic of China.
Org Lett. 2019 Aug 2;21(15):6040-6044. doi: 10.1021/acs.orglett.9b02199. Epub 2019 Jul 23.
A copper-catalyzed intramolecular enantioselective and diastereoselective borylative coupling of styrenes and ketones was achieved by merging desymmetrization strategy and olefin difunctionalization. The reaction proceeds through an initial enantioselective borylcupration of styrenes, followed by a highly selective direct addition to 1,3-diketones. The bicyclic scaffolds with three chiral carbon centers, including two tetrasubstituted carbons, were generated in excellent yields, diastereoselectivities, and enantioselectivities. This catalytic tandem reaction has great potential for further synthetic application of the chiral polycyclic compounds, because of the versatility of the functional groups in the products.
通过结合去对称化策略和烯烃双官能团化反应，实现了铜催化的苯乙烯与酮的分子内对映选择性和非对映选择性硼化偶联反应。该反应首先通过苯乙烯的对映选择性硼铜化反应进行，随后是对1,3 - 二酮的高度选择性直接加成反应。具有三个手性碳中心（包括两个四取代碳）的双环骨架以优异的产率、非对映选择性和对映选择性生成。由于产物中官能团的多样性，这种催化串联反应在手性多环化合物的进一步合成应用中具有巨大潜力。
