Synthesis of Axially Chiral Biaryls through Sulfoxide-Directed Asymmetric Mild C-H Activation and Dynamic Kinetic Resolution
Synthesis of Axially Chiral Biaryls through Sulfoxide-Directed Asymmetric Mild C-H Activation and Dynamic Kinetic Resolution
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DOI：
10.1002/anie.201407865
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发表时间：
2014-12-08
影响因子：
16.6
通讯作者：
Colobert, Francoise
中科院分区：
文献类型：
--
作者：
Hazra, Chinmoy Kumar;Dherbassy, Quentin;Colobert, Francoise
一种温和而稳健的直接CH官能化策略被应用于轴向手性联芳化合物的合成。这种有效的和立体选择性的转化通过原始的动态动力学拆分途径发生，使得非预官能化底物的非对映异构体混合物能够转化为阻转异构体纯的高度取代的联芳基支架。这种转化的主要特点是使用对映体纯亚砜作为手性辅助基团和无痕导向基团。进一步说明了新合成的联芳基化合物作为有价值的结构单元的潜力。
A mild and robust direct CH functionalization strategy has been applied to the synthesis of axially chiral biaryls. Such an efficient and stereoselective transformation occurs through an original dynamic kinetic resolution pathway enabling the conversion of diastereomeric mixtures of non-prefunctionalized substrates into atropisomerically pure, highly substituted biaryl scaffolds. The main feature of this transformation is the use of an enantiopure sulfoxide as both chiral auxiliary and traceless directing group. The potential of newly synthesized biaryls as valuable building blocks is further illustrated.