Cho Soo Min, Kim Jae Yeon, Han Shinyeong, Ryu Do Hyun
Department of Chemistry, Sungkyunkwan University, 300 Cheoncheon, Jangan, Suwon 16419, Korea.
J Org Chem. 2022 Aug 19;87(16):11196-11203. doi: 10.1021/acs.joc.2c01527. Epub 2022 Jul 30.
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.
本文描述了一种用于手性1,2-氨基叔醇的可见光介导合成方法的开发。在手性恶唑硼烷鎓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对芳基甲基酮的对映选择性加成反应能够以高收率（高达88%）和优异的对映选择性（高达98% ee）提供手性1,2-氨基叔醇衍生物。通过自由基捕获分析、自由基钟分析和量子产率测量等机理研究，提出了一个合理的催化循环。
