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Construction of Cyclic Sulfamidates Bearing Two gem-Diaryl Stereocenters through a Rhodium-Catalyzed Stepwise Asymmetric Arylation Protocol
- Zhang, Yu-Fang, Chen, Diao, Chen, Wen-Wen, Xu, Ming-Hua
- Organic letters 2016 v.18 no.11 pp. 2726-2729
- acids, arylation, chemical structure, ketimines, ligands
- A rhodium-catalyzed stepwise asymmetric 1,4- and 1,2-addition of arylboronic acids to α,β-unsaturated cyclic N-sulfonyl ketimines has been developed, providing a wide range of gem-diaryl-substituted chiral benzosulfamidates with high optical purities. C₁-Symmetric chiral diene and branched chiral sulfur–olefin ligands were sequentially utilized in this double-arylation process for high stereocontrol. Further synthetic utility offers new opportunities for the facile construction of otherwise difficult to access polycyclic heterocycles.