Journal
ORGANIC LETTERS
Volume 20, Issue 18, Pages 5770-5773Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.8b02468
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Funding
- EPSRC
- Bristol Centre for Doctoral Training in Chemical Synthesis
- AstraZeneca through a CASE award
- Deutsche Forschungsgemeinschaft [LE 3853/1-1]
- Engineering and Physical Sciences Research Council [EP/K03927X/1] Funding Source: researchfish
- EPSRC [EP/L018527/2, EP/K03927X/1] Funding Source: UKRI
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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.
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