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Iridium-catalyzed aza-spirocyclization of indole-tethered amides: an interrupted pictet–spengler reaction

DOI: 10.1021/acs.orglett.9b02194 DOI Help

Authors: Pablo Gabriel (University of Oxford) , Alex W. Gregory (University of Oxford) , Darren J. Dixon (University of Oxford)
Co-authored by industrial partner: No

Type: Journal Paper
Journal: Organic Letters

State: Published (Approved)
Published: August 2019

Open Access Open Access

Abstract: A mild, reductive spirocyclization of indole-linked amides and lactams for the efficient and selective synthesis of aza-spirocyclic indoline products is described. The catalytic reductive activation of tertiary amides or lactams by Vaska’s complex with tetramethyldisiloxane as the terminal reductant allowed iminium ion formation, before a diastereoselective 5-endo-trig spirocyclization of the tethered indole moiety was triggered. Terminal reduction affords the aza-spiroindoline products in an overall highly chemoselective and diastereoselective one-pot process.

Subject Areas: Chemistry

Technical Areas: