Pd-Catalyzed Asymmetric Dearomative Arylation of Indoles via a Desymmetrization Strategy
Yu-Han Nie1,2, Masaaki Komatsuda3, Ping Yang2
1Chang-Kung Chuang Institute, East China Normal University, Shanghai 200062, China.
Abstract:
Pd-catalyzed asymmetric dearomative arylation of C3-substituted indoles is realized via a desymmetrization strategy. A BINOL-derived chiral phosphoramidite ligand is found to be highly efficient for the stereoselective control in this reaction. This method provides a convenient synthesis of spiroindolenines bearing two stereogenic centers in good yields (up to 98%) with excellent diastereo- and enantioselectivities (up to >20:1 dr and 97% ee), which could also be applied in asymmetric dearomative arylation of the simple C3-tethered indoles.
Related Concept Videos
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry
[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation


