N,N'-二氧代/Gd(OTf) 配合物促进的硅基烯酮亚胺与靛红的不对称Aldol 反应：水起重要作用。
N, N'-Dioxide/Gd(OTf) Complex-Promoted Asymmetric Aldol Reaction of Silyl Ketene Imines with Isatins: Water Plays an Important Role.
机构信息
Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry , Sichuan University , Chengdu 610064 , China.
出版信息
Org Lett. 2018 Sep 7;20(17):5314-5318. doi: 10.1021/acs.orglett.8b02239. Epub 2018 Aug 23.
A highly diastereo- and enantioselective aldol reaction of isatins with silyl ketene imines was realized by using a chiral N, N'-dioxide/Gd complex (1 mol %), and with the addition of water, all the reactions completed within 10 min and various β-hydroxy nitriles with adjacent tetrasubstituted stereocenters were obtained in excellent outcomes. The essential role of water was probed, and a possible transition state model was proposed based on an eight-coordinated N, N'-dioxide/Gd complex.
手性 N, N'-二氧化物/Gd 配合物（1 摩尔%）的使用实现了靛红与硅烯酮亚胺的高度非对映选择性和对映选择性的 aldol 反应，并且添加水后，所有反应在 10 分钟内完成，得到了各种具有相邻四取代立体中心的 β-羟基腈，产率优异。考察了水的重要作用，并基于八配位 N, N'-二氧化物/Gd 配合物提出了一个可能的过渡态模型。
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