C2-Symmetric Bicyclic Bisborane Catalysts: Kinetic or Thermodynamic Products of a Reversible Hydroboration of Dienes
Xian-Shuang Tu
State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry and Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University, 94 Weijin Road, Tianjin, 300071 China
Search for more papers by this authorNing-Ning Zeng
State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry and Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University, 94 Weijin Road, Tianjin, 300071 China
Search for more papers by this authorRu-Ye Li
State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry and Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University, 94 Weijin Road, Tianjin, 300071 China
Search for more papers by this authorYu-Quan Zhao
State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry and Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University, 94 Weijin Road, Tianjin, 300071 China
Search for more papers by this authorDe-Zhen Xie
State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry and Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University, 94 Weijin Road, Tianjin, 300071 China
Search for more papers by this authorCorresponding Author
Prof. Dr. Qian Peng
State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry and Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University, 94 Weijin Road, Tianjin, 300071 China
Search for more papers by this authorCorresponding Author
Prof. Dr. Xiao-Chen Wang
State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry and Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University, 94 Weijin Road, Tianjin, 300071 China
Search for more papers by this authorXian-Shuang Tu
State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry and Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University, 94 Weijin Road, Tianjin, 300071 China
Search for more papers by this authorNing-Ning Zeng
State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry and Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University, 94 Weijin Road, Tianjin, 300071 China
Search for more papers by this authorRu-Ye Li
State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry and Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University, 94 Weijin Road, Tianjin, 300071 China
Search for more papers by this authorYu-Quan Zhao
State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry and Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University, 94 Weijin Road, Tianjin, 300071 China
Search for more papers by this authorDe-Zhen Xie
State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry and Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University, 94 Weijin Road, Tianjin, 300071 China
Search for more papers by this authorCorresponding Author
Prof. Dr. Qian Peng
State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry and Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University, 94 Weijin Road, Tianjin, 300071 China
Search for more papers by this authorCorresponding Author
Prof. Dr. Xiao-Chen Wang
State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry and Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University, 94 Weijin Road, Tianjin, 300071 China
Search for more papers by this authorGraphical Abstract
B,B bicycles: A new class of C2-symmetric bicyclic bisborane catalysts was synthesized by treating bicyclic dienes with HB(C6F5)2 or HB(p-C6F4H)2. Remarkably, two diastereomeric catalysts could be accessed selectively from a single diene precursor by simply varying the reaction temperature (see scheme). These catalysts exhibited excellent activity and selectivity in the hydrogenation of imines.
Abstract
We prepared a new class of chiral C2-symmetric bicyclic bisborane catalysts by addition reactions of internal dienes with the Piers borane, HB(C6F5)2, and an analogue, HB(p-C6F4H)2. The dependence of the addition pattern on the reaction temperature allowed us to selectively prepare two diastereomeric catalysts from a single diene precursor. The bisboranes prepared in situ exhibited excellent activity (turnover numbers up to 200 at −40 °C) and enantioselectivity (up to 95 % ee) in imine hydrogenation reactions.
Supporting Information
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Citing Literature
November 12, 2018
Pages 15096-15100
