当前位置: X-MOL 学术J. Org. Chem. › 论文详情
Our official English website, www.x-mol.net, welcomes your feedback! (Note: you will need to create a separate account there.)
Visible Light-Mediated Enantioselective Addition of α-Aminoalkyl Radicals to Ketones Catalyzed by Chiral Oxazaborolidinium Ion
The Journal of Organic Chemistry ( IF 3.6 ) Pub Date : 2022-07-30 , DOI: 10.1021/acs.joc.2c01527
Soo Min Cho 1 , Jae Yeon Kim 1 , Shinyeong Han 1 , Do Hyun Ryu 1
Affiliation  

The development of a visible light-mediated synthetic method for chiral 1,2-amino tertiary alcohols is described. In the presence of a chiral oxazaborolidinium ion catalyst and photosensitizer, the enantioselective addition of an α-aminoalkyl radical to aryl methyl ketones under visible light provides chiral 1,2-amino tertiary alcohol derivatives in high yields (up to 88%) with excellent enantioselectivities (up to 98% ee). With mechanistic studies such as radical trapping analysis, radical clock analysis, and the measurement of quantum yield, a plausible catalytic cycle is proposed.

中文翻译:

手性恶氮硼烷离子催化的可见光介导的α-氨基烷基自由基对酮的对映选择性加成

描述了一种可见光介导的手性 1,2-氨基叔醇合成方法的发展。在手性 oxazaborolidinium 离子催化剂和光敏剂存在下,α-氨基烷基自由基在可见光下与芳基甲基酮的对映选择性加成以高产率(高达 88%)提供手性 1,2-氨基叔醇衍生物,并具有优异的对映选择性(高达 98% ee)。通过自由基捕获分析、自由基时钟分析和量子产率测量等机理研究,提出了一种合理的催化循环。
更新日期:2022-07-30
down
wechat
bug