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Copper-catalyzed aerobic oxidative radical alkoxycyclization of tryptamines to access 3-alkoxypyrroloindolines.

ABSTRACT: We report a copper-catalyzed alkoxycyclization of tryptamine derivatives with O₂ as the sole oxidant, leading to a variety of C3a-alkoxypyrroloindolines in good yields with high diastereoselectivities. This reaction involves an interesting double catalytic cycle in which copper-catalyzed carboamination cyclization is favored to form the C-3 radical pyrrolidinoindoline intermediate, then a copper-catalytic radical alkoxylation reaction proceeds smoothly.

SUBMITTER: Wang W

PROVIDER: S-EPMC9033248 | biostudies-literature | 2021 May

REPOSITORIES: biostudies-literature

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Copper-catalyzed aerobic oxidative radical alkoxycyclization of tryptamines to access 3-alkoxypyrroloindolines.

Wang Wei W Song Jun-Rong JR Li Zhi-Yao ZY Zhong Ting T Chi Qin Q Ren Hai H Pan Wei-Dong WD

RSC advances 20210519 29

We report a copper-catalyzed alkoxycyclization of tryptamine derivatives with O<sub>2</sub> as the sole oxidant, leading to a variety of C3a-alkoxypyrroloindolines in good yields with high diastereoselectivities. This reaction involves an interesting double catalytic cycle in which copper-catalyzed carboamination cyclization is favored to form the C-3 radical pyrrolidinoindoline intermediate, then a copper-catalytic radical alkoxylation reaction proceeds smoothly. ...[more]

PMID: 35480191

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