钌
对映选择合成
化学
催化作用
羧酸
组合化学
不对称诱导
立体化学
有机化学
药物化学
作者
Uttam Dhawa,Robert Connon,João C. A. Oliveira,Ralf Steinbock,Lutz Ackermann
出处
期刊:Organic Letters
[American Chemical Society]
日期:2021-03-17
卷期号:23 (7): 2760-2765
被引量:38
标识
DOI:10.1021/acs.orglett.1c00615
摘要
Asymmetric ruthenium-catalyzed C–H alkylations were enabled by a chiral C2-symmetric carboxylic acid. The mild cooperative ruthenium(II) catalysis set the stage for the assembly of chiral tetrahydrocarbazoles and cyclohepta[b]indoles with high levels of enantioselectivity at room temperature. Mechanistic studies by experiment and computation identified a fast C–H ruthenation, along with a rate- and enantio-determining proto-demetalation. The asymmetric induction was governed by weak attractive secondary dispersion interactions as found in NCI analysis of the key transition states.
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