Copper(I)-Catalyzed Indolyl Ynamide Oxidation/Dearomatization: Divergent and Regioselective Synthesis of Valuable Indoline Scaffolds
Document Type
Article
Publication Date
4-28-2024
Department
College of Forest Resources and Environmental Science
Abstract
A highly convenient copper(I)-catalyzed oxidation-initiated cyclopropanation of indolyl ynamide for the rapid construction of indole-fused cyclopropane-lactams is described, which represents, to the best of our knowledge, the first non-noble-metal-catalyzed indolyl ynamide oxidation/dearomatization by the in situ generated α-oxo copper carbenes. Compared to hydrazone and diazo, the use of alkynes as carbene precursors allows cyclopropanation to occur under a safe and convenient pathway. Moreover, this transformation can lead to the divergent synthesis of pentacyclic spiroindolines involving the reversal of ynamide regioselectivity by engineering substrate structures.
Publication Title
Organic letters
Recommended Citation
Ru, G.,
Liu, Q.,
Wei, K.,
Zhu, X.,
Jiang, X.,
Xie, L.,
Su, H.,
Lv, D.,
Xie, X.,
&
Shen, W.
(2024).
Copper(I)-Catalyzed Indolyl Ynamide Oxidation/Dearomatization: Divergent and Regioselective Synthesis of Valuable Indoline Scaffolds.
Organic letters.
http://doi.org/10.1021/acs.orglett.4c00719
Retrieved from: https://digitalcommons.mtu.edu/michigantech-p2/725