Rhodium(III)/Chiral Carboxylic Acid Catalyzed Enantioselective C(sp3)-H Alkylation of 8-Ethylquinolines with α,β-Unsaturated Carbonyl Compounds
Rhodium(III)/Chiral Carboxylic Acid Catalyzed Enantioselective C(sp3)-H Alkylation of 8-Ethylquinolines with α,β-Unsaturated Carbonyl Compounds
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DOI：
10.1021/acs.orglett.0c02872
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发表时间：
2020-11-06
期刊：
影响因子：
5.2
通讯作者：
Matsunaga, Shigeki
中科院分区：
文献类型：
--
作者：
Huang, Long-Tao;Fukagawa, Seiya;Matsunaga, Shigeki
描述了用Rh-III催化剂和手性羧酸与烯酮或丙烯醛进行8-乙基喹啉的对映选择性C-H烷基化反应。在温和的反应条件下，以二萘基为基础的手性羧酸能够对8-乙基喹啉C(sp(3))-H键进行对映选择性裂解。得到的结果表明，高价9族金属催化剂和手性羧酸的组合在对映选择性C(sp(3))-H活化和随后的C-C键形成中具有实用性。
The enantioselective C-H alkylation of 8-ethylquinolines with enones or acrolein using a Rh-III catalyst and a chiral carboxylic acid is described. Under mild reaction conditions, a binaphthyl-based chiral carboxylic acid enables the enantioselective cleavage of the 8-ethylquinoline C(sp(3))-H bond. The obtained results demonstrate the utility of the combination of a high-valent group 9 metal catalyst and a chiral carboxylic acid for the enantioselective C(sp(3))-H activation and the subsequent C-C bond formation.