Silver-Catalyzed Asymmetric Dearomatization of Electron-Deficient Heteroarenes via Interrupted Barton-Zard Reaction

Herein we report a catalytic asymmetric dearomatization reaction of electron-deficient heteroarenes with alpha-substituted isocyanoacetates through an interrupted Barton-Zard reaction. A range of optically active pyrrolo[3,4-b]indole derivatives was obtained in good yields (up to 97 %) with high stereoselectivities (up to >20:1 dr and 97 % ee), using a catalytic system consisting of a cinchona-derived amino-phosphine and silver oxide. This reaction features wide substrate scope and mild conditions, and provides a new strategy for developing asymmetric dearomatization reactions.

Automated summary

In this study, a catalytic asymmetric dearomatization reaction of electron-deficient heteroarenes with alpha-substituted isocyanoacetates was reported, leading to a range of optically active pyrrolo[3,4-b]indole derivatives. The reaction yielded good results with high stereoselectivities, using a catalytic system consisting of a cinchona-derived amino-phosphine and silver oxide. This method features wide substrate scope, mild conditions, and provides a new strategy for developing asymmetric dearomatization reactions.