Catalytic (3 + 2) annulation of donor-acceptor aminocyclopropane monoesters and indoles.

Chem Sci

Laboratory of Catalysis and Organic Synthesis, Institut des Sciences et Ingénierie Chimique, Ecole Polytechnique Fédérale de Lausanne Ch-1015 Lausanne Switzerland

Published: July 2021

The efficient catalytic activation of donor-acceptor aminocyclopropanes lacking the commonly used diester acceptor is reported here in a (3 + 2) dearomative annulation with indoles. Bench-stable tosyl-protected aminocyclopropyl esters were converted into cycloadducts in 46-95% yields and up to 95 : 5 diastereomeric ratio using catalytic amounts of triethylsilyl triflimide. Tricyclic indoline frameworks containing four stereogenic centers including all-carbon quaternary centers were obtained.

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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC8246098PMC
http://dx.doi.org/10.1039/d1sc01127hDOI Listing

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