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手性含氧杂环的铜催化不对称去对称芳基 C-O 偶联反应的对映选择性合成。

Enantioselective Synthesis of Chiral Oxygen-Containing Heterocycles Using Copper-Catalyzed Aryl C-O Coupling Reactions via Asymmetric Desymmetrization.

机构信息

College of Chemical and Pharmaceutical Engineering, Hebei University of Science and Technology , Shijiazhuang, 050018, China.

College of Pharmacy, Jinan University , No. 601 Huangpu Avenue West, Guangzhou, 510632, China.

出版信息

J Org Chem. 2017 Feb 3;82(3):1458-1463. doi: 10.1021/acs.joc.6b02646. Epub 2017 Jan 20.

Abstract

An enantioselective desymmetric aryl C-O coupling reaction was demonstrated under the catalysis of CuI and a chiral cyclic diamine ligand. A series of chiral oxygen-containing heterocyclic units such as 2,3-dihydrobenzofurans, chromans, and 1,4-benzodioxanes with tertiary or quaternary stereocarbon centers were synthesized with this method. DFT calculations were also carried out for a better understanding of the model for enantiocontrol.

摘要

手性铜催化的不对称去对称芳基 C-O 偶联反应

在 CuI 和手性环状二胺配体的催化下,实现了不对称去对称芳基 C-O 偶联反应。该方法合成了一系列具有三级或季碳中心的手性含氧杂环单元,如 2,3-二氢苯并呋喃、色满和 1,4-苯并二恶烷。为了更好地理解对映控制模型,还进行了 DFT 计算。

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