Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 50, Pages 13740-13745Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201407677
Keywords
asymmetric catalysis; electrocyclic reactions; one-pot processes; tandem reaction; thioureas
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Funding
- 973 program [2015CB856600]
- NSFC [21172075, 21222204]
- Program of SSCS [13XD1401600]
- Ministry of Education (PCSIRT) [NCET-11-0147]
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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 insitu 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 BrOnsted acid catalyzed ketimine formation reaction. The electrocyclization was catalyzed by a bifunctional chiral BrOnsted base/hydrogen bond donor catalyst. The one-pot process gave the desired products in good yields and with excellent enantioselectivity.
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