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Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
Spiro-[indene-1,2'-indolin] scaffolds via Rh(III) catalyzed C-H activation/[3+2] spiroannulation
Imtiaj Mondal1, Gracy Salam1, Sudip Karmakar1
1Organic and Medicinal Chemistry Division, CSIR-Indian Institute of Chemical Biology, 4-Raja S. C. Mullick Road, Jadavpur, Kolkata 700032, India. imtiaj612@gmail.com.
Abstract:
An unprecedented [3+2] spiroannulation of 3,3-dimethyl-2-aryl-3H-indole with ynones/ynoates has been exemplified, furnishing architecturally ornamented C2-spiro-[indene-1,2'-indolin] scaffolds bearing an all-carbon C3-quaternary center proceeding via a Rh(III) catalytic cycle. The protocol exhibits broad substrate generality and good functional-group tolerance, and enables the facile incorporation of natural-product-derived ynoates, delivering the products in good to excellent yields and enabling the development of potential biologically relevant spirocyclic scaffolds.
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