Asymmetric Borylative Propargylation of Ketones Catalyzed by a Copper(I) Complex
Asymmetric Borylative Propargylation of Ketones Catalyzed by a Copper(I) Complex
复制标题
铜(I)配合物催化酮的不对称硼基丙炔化
DOI：
10.1021/acs.orglett.8b03912
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发表时间：
2019-02-15
期刊：
影响因子：
5.2
通讯作者：
Yin, Liang
中科院分区：
文献类型：
--
作者：
Gan, Xu-Cheng;Yin, Liang
本发明公开了一种铜(I)催化的单酮不对称硼化丙烷化反应。添加剂NaBARF被发现是实现良好的对映选择性的关键。该反应具有底物范围广、官能团耐受性好、非对映选择性和对映体选择性高、反应稳健性好等优点。在钯催化的Suzuki-Miyaura反应中，硼化产物作为合适的交叉偶联伙伴。最后，以手性哌啶类化合物的不对称合成为例说明了该方法的合成实用性。
A copper(I)-catalyzed asymmetric borylative propargylation of simple ketones was disclosed. Additive NaBARF was found to be pivotal to achieve excellent enantioselectivity. This reaction enjoyed advantages of broad substrate scope, good tolerance of functional groups, high diastereo- and enantioselectivities, and reaction robustness. The borylative product served as a suitable cross-coupling partner in a palladium-catalyzed Suzuki-Miyaura reaction. Finally, the synthetic utility of the methodology was showcased by the asymmetric synthesis of a chiral piperidine derivative.