Chiral Amino Alcohol Accelerated and Stereocontrolled Allylboration of Iminoisatins: Highly Efficient Construction of Adjacent Quaternary Stereogenic Centers.
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.
Innovative Drug Research Centre, School of Pharmaceutical Sciences, Chongqing University, 55 Daxuecheng South Road, Shapingba, Chongqing, 401331, China.
Qiuyuan
Q
Tan
Innovative Drug Research Centre, School of Pharmaceutical Sciences, Chongqing University, 55 Daxuecheng South Road, Shapingba, Chongqing, 401331, China.
Xinqiao
X
Wang
Innovative Drug Research Centre, School of Pharmaceutical Sciences, Chongqing University, 55 Daxuecheng South Road, Shapingba, Chongqing, 401331, China.
Yang
Y
Xiong
Innovative Drug Research Centre, School of Pharmaceutical Sciences, Chongqing University, 55 Daxuecheng South Road, Shapingba, Chongqing, 401331, China.
Zimeng
Z
Zhao
Innovative Drug Research Centre, School of Pharmaceutical Sciences, Chongqing University, 55 Daxuecheng South Road, Shapingba, Chongqing, 401331, China.
Lu
L
Li
Innovative Drug Research Centre, School of Pharmaceutical Sciences, Chongqing University, 55 Daxuecheng South Road, Shapingba, Chongqing, 401331, China.
Pei
P
Tang
Innovative Drug Research Centre, School of Pharmaceutical Sciences, Chongqing University, 55 Daxuecheng South Road, Shapingba, Chongqing, 401331, China.
Min
0000-0002-3851-7836
M
Zhang
3-aminooxindoles; allylboronic acids; amino alcohols; asymmetric allylation; quaternary stereogenic centers