Journal
RSC ADVANCES
Volume 11, Issue 29, Pages 18080-18083Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d1ra02679h
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Funding
- NSFC [22061010]
- Guizhou Province Science and Technology Foundation, China [QKHJC[2019]1214]
- CAS Light of West China Program
- Guizhou Provincial Thousands of Innovative and Entrepreneurial Talents program [GZQ202006080]
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A copper-catalyzed alkoxycyclization of tryptamine derivatives with O-2 as the oxidant has been developed, providing a variety of C3a-alkoxypyrroloindolines in good yields with high diastereoselectivities. The reaction involves a double catalytic cycle with copper-catalyzed carboamination cyclization followed by a copper-catalyzed radical alkoxylation reaction.
We report a copper-catalyzed alkoxycyclization of tryptamine derivatives with O-2 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.
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