The 3-lithiated indole is generated from silylindole 1 by treatment with alkyllithium and when allowed to react at -78°C with various electrophiles, regioselectively yields 3-substituted indoles in good yield . This is because the lithiated intermediate contains a bulky triisopropylsilyl group at the 1-position. The steric bulk provides protection at the 2-position of indole which prevent 3→2 migration of lithium and subsequent ring fragmentation1).
Reported applications of 1 are the synthesis of tryptophan2) and the total synthesis of grossularine-13) which is a type of alkaloid.
Caution Notice
It has come to our notice that certain fraudulent individuals or entities are misusing our Company’s name and TCI’s registered trademarks by promoting and offering regulated and hazardous chemical substances through online platforms like YouTube. We hereby categorically clarify that TCI has no association or connection whatsoever with the products being displayed or sold in the videos. These products have been falsely represented as being associated with TCI, and the unauthorized use of our trademark and brand name is both illegal and misleading. TCI Chemicals markets and sells its products exclusively through its official website and authorized distributors. If you become aware of any such fraudulent activity or require clarification, you may reach out to us at: Sales-IN@TCIchemicals.com. Click Here to View the Caution Notice.
Product Document Searching Made Easy by 2D Code! | [Product Highlights] Endogenous Biotin-Blocking Reagent...