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The base-promoted dearomatizing cyclization of anionic indole-containing urea derivatives provided tri- or tetracyclic indoline-containing scaffolds from lithiated urea intermediates. 3-Substituted indoles, including tryptamine derivatives, generally underwent the reaction in high yield and with excellent diastereoselectivity. In situ IR spectroscopy suggests a deprotonation-carbolithiation-reprotonation mechanism.
- BCS and TECS CDTs
Hill, J. E., Lefebvre, Q., Fraser, L. A., & Clayden, J. (2018). Polycyclic Indoline Derivatives by Dearomatizing Anionic Cyclization of Indole and Tryptamine-Derived Ureas. Organic Letters, 20(18), 5770-5773. https://doi.org/10.1021/acs.orglett.8b02468