The atroposelective electrophilicamination of indoles catalyzed by a chiral phosphoric acid (CPA) is reported. The reaction proceeds by asymmetric 1,6-addition to p-quinone diimines to deliver atropochiral N-sulfonyl-3-arylaminoindoles in good yields and with excellent ee values.
报道了手性磷酸(CPA)催化的吲哚选择性亲电胺化。该反应通过不对称的 1,6-加成与对醌二亚胺进行,以良好的收率和优异的 ee 值提供非手性N-磺酰基-3-芳基氨基吲哚。
Organocatalytic Enantioselective Synthesis of Atropisomeric Aryl‐
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‐Quinones: Platform Molecules for Diversity‐Oriented Synthesis of Biaryldiols
作者:Ye‐Hui Chen、Heng‐Hui Li、Xiao Zhang、Shao‐Hua Xiang、Shaoyu Li、Bin Tan
DOI:10.1002/anie.202004671
日期:2020.7.6
Presented here is a class of novel axiallychiral aryl‐p ‐quinones as platform molecules for the preparation of non‐C2symmetric biaryldiols. Two sets of aryl‐p ‐quinone frameworks were synthesized with remarkable enantiocontrol by means of chiral phosphoric acid catalyzed enantioselective arylation of p ‐quinones by central‐to‐axialchirality conversion. These aryl‐p ‐quinones were then used to access