Dearomatization of 2,3-Disubstituted Indoles via 1,8-Addition of Propargylic (Aza)-para-Quinone Methides

Dearomatization of indole is a useful strategy to access indolimines: a motif widely exists in biologically active molecules and natural products. Herein, an efficient method for the dearomatization of 2,3-disubstituted indoles to generate diverse indolimines with tetrasubstituted allenes is described. This work accomplishes dearomatization of 2,3-disubstituted indoles through 1,8-addition of (aza)-para-quinone methides, which are generated in situ from propargylic alcohols. A series of synthetically useful indolimines containing quaternary carbon centers and tetrasubstituted allenes can be accessed in good yields (up to 99%). Additionally, the separability of product isomers, diversified product transformations, and easy scale-up of the reaction demonstrate the potential application of this method.

Automated summary

This study presents an efficient method for dearomatization of 2,3-disubstituted indoles to access diverse indolimines with quaternary carbon centers and tetrasubstituted allenes through 1,8-addition of (aza)-para-quinone methides. The products can be obtained in good yields (up to 99%) with separability of isomers, diversified product transformations, and easy scale-up potential, showcasing the method's applicability.