摘要
The single-electron transfer-induced oxidative transformation of indoles has been extensively explored in recent years.However,research toward high enantioselective control in this reaction is rare.Herein,we report an enantioselective catalytic single-electron transfer-induced oxidative rearrangement of cyclic indoles enabled by dual chiral copper/phosphoric acid catalysis.Using atmospheric oxygen(O_(2))as the terminal oxidant,the reactions of tetrahydro-β-carbolines,tetrahydropyrano[3,4-b]indoles and the challenging tetrahydrocarbazoles are all realized,providing diverse rearrangement products including pyrrolidinyl-,tetrahydrofuranyl-and cyclopentyl-bearing spiroindolinones in good yields with high enantioselectivities.The synthetic utility of this protocol was demonstrated in a concise synthesis of(+)-coerulescine and(+)-horsfiline.These findings would provide new insights and opportunities for future asymmetric oxidative radical reaction design.
基金
the National Natural Science Foundation of China(Nos.22261010,22201053,22461012)
Guizhou Provincial Major Scientific and Technological Program,China(No.QKHZDZX[2024]015)for financial support。
