Asymmetric triple relay catalysis: enantioselective synthesis of spirocyclic indolines through a one-pot process featuring an asymmetric 6π electrocyclization.

Angew Chem Int Ed Engl

Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663N, Zhongshan Road, Shanghai 200062 (China).

Published: December 2014

A rare example of a one-pot process that involves asymmetric triple relay catalysis is reported. The key step is an asymmetric [1,5] electrocyclic reaction of functionalized ketimines. The substrates for this process were obtained in situ in a two-step process that involved the hydrogenation of nitroarenes with a Pd/C catalyst to yield aryl amines and their subsequent coupling with isatin derivatives in a Brønsted acid catalyzed ketimine formation reaction. The electrocyclization was catalyzed by a bifunctional chiral Brønsted base/hydrogen bond donor catalyst. The one-pot process gave the desired products in good yields and with excellent enantioselectivity.

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http://dx.doi.org/10.1002/anie.201407677DOI Listing

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