Chiral Amino Alcohol Accelerated and Stereocontrolled Allylboration of Iminoisatins: Highly Efficient Construction of Adjacent Quaternary Stereogenic Centers
Qiuyuan Tan
Innovative Drug Research Centre, School of Pharmaceutical Sciences, Chongqing University, 55 Daxuecheng South Road, Shapingba, Chongqing, 401331 China
Search for more papers by this authorXinqiao Wang
Innovative Drug Research Centre, School of Pharmaceutical Sciences, Chongqing University, 55 Daxuecheng South Road, Shapingba, Chongqing, 401331 China
Search for more papers by this authorYang Xiong
Innovative Drug Research Centre, School of Pharmaceutical Sciences, Chongqing University, 55 Daxuecheng South Road, Shapingba, Chongqing, 401331 China
Search for more papers by this authorZimeng Zhao
Innovative Drug Research Centre, School of Pharmaceutical Sciences, Chongqing University, 55 Daxuecheng South Road, Shapingba, Chongqing, 401331 China
Search for more papers by this authorLu Li
Innovative Drug Research Centre, School of Pharmaceutical Sciences, Chongqing University, 55 Daxuecheng South Road, Shapingba, Chongqing, 401331 China
Search for more papers by this authorPei Tang
Innovative Drug Research Centre, School of Pharmaceutical Sciences, Chongqing University, 55 Daxuecheng South Road, Shapingba, Chongqing, 401331 China
Search for more papers by this authorCorresponding Author
Prof. Dr. Min Zhang
Innovative Drug Research Centre, School of Pharmaceutical Sciences, Chongqing University, 55 Daxuecheng South Road, Shapingba, Chongqing, 401331 China
Search for more papers by this authorQiuyuan Tan
Innovative Drug Research Centre, School of Pharmaceutical Sciences, Chongqing University, 55 Daxuecheng South Road, Shapingba, Chongqing, 401331 China
Search for more papers by this authorXinqiao Wang
Innovative Drug Research Centre, School of Pharmaceutical Sciences, Chongqing University, 55 Daxuecheng South Road, Shapingba, Chongqing, 401331 China
Search for more papers by this authorYang Xiong
Innovative Drug Research Centre, School of Pharmaceutical Sciences, Chongqing University, 55 Daxuecheng South Road, Shapingba, Chongqing, 401331 China
Search for more papers by this authorZimeng Zhao
Innovative Drug Research Centre, School of Pharmaceutical Sciences, Chongqing University, 55 Daxuecheng South Road, Shapingba, Chongqing, 401331 China
Search for more papers by this authorLu Li
Innovative Drug Research Centre, School of Pharmaceutical Sciences, Chongqing University, 55 Daxuecheng South Road, Shapingba, Chongqing, 401331 China
Search for more papers by this authorPei Tang
Innovative Drug Research Centre, School of Pharmaceutical Sciences, Chongqing University, 55 Daxuecheng South Road, Shapingba, Chongqing, 401331 China
Search for more papers by this authorCorresponding Author
Prof. Dr. Min Zhang
Innovative Drug Research Centre, School of Pharmaceutical Sciences, Chongqing University, 55 Daxuecheng South Road, Shapingba, Chongqing, 401331 China
Search for more papers by this authorAbstract
We have developed a highly efficient asymmetric allylboration of ketimines with nonchiral γ,γ-disubstituted allylboronic acids by using a chiral amino alcohol as the directing group, which is otherwise challenging. The amino alcohol not only serves as a cheap source of nitrogen and chirality, but also dramatically enhances the reactivity. The versatility of this method was demonstrated by its ability to access all four stereoisomers with adjacent quaternary carbon centers. A reaction model was proposed to explain the diastereoselectivity and the rate-accelerating effect.
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