Yoon Wan Seok, Jang Won Jun, Yoon Woojin, Yun Hoseop, Yun Jaesook
Department of Chemistry and Institute of Basic Science, Sungkyunkwan University, Suwon, 16419, Korea.
Department of Chemistry, Dong-A University, Busan, 49315, Korea.
Nat Commun. 2022 May 11;13(1):2570. doi: 10.1038/s41467-022-30286-8.
Asymmetric construction of C(sp)-C(sp) bond with good stereocontrol of the two connecting carbon centres retaining all carbon or hydrogen substituents is a challenging target in transition metal catalysis. Transition metal-catalysed reductive coupling of unsaturated π-substrates is considered as a potent tool to expediently develop the molecular complexity with high atom efficiency. However, such an asymmetric and intermolecular process has yet to be developed fully. Herein, we report an efficient strategy to reductively couple two prochiral conjugate alkenes using a copper-catalysed tandem protocol in the presence of diboron. Notably, this transformation incorporates a wide range of terminal and internal enynes as coupling partners and facilitates highly diastereo- and enantioselective synthesis of organoboron derivatives with multiple adjacent stereocentres in a single operation.
在过渡金属催化中，构建具有良好立体控制的C(sp)-C(sp)键，同时保留两个连接碳中心上的所有碳或氢取代基，是一个具有挑战性的目标。过渡金属催化的不饱和π底物的还原偶联被认为是一种高效的工具，能够以高原子效率快速增加分子复杂性。然而，这种不对称的分子间过程尚未得到充分发展。在此，我们报道了一种有效的策略，即在联硼存在下，使用铜催化的串联反应将两个前手性共轭烯烃进行还原偶联。值得注意的是，这种转化反应纳入了多种末端和内烯炔作为偶联伙伴，并能在一步反应中高效地实现具有多个相邻立体中心的有机硼衍生物的非对映和对映选择性合成。
