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- Title
Asymmetric Triple Relay Catalysis: Enantioselective Synthesis of Spirocyclic Indolines through a One-Pot Process Featuring an Asymmetric 6π Electrocyclization.
- Authors
Yin, Xiao-Ping; Zeng, Xing-Ping; Liu, Yun-Lin; Liao, Fu-Min; Yu, Jin-Sheng; Zhou, Feng; Zhou, Jian
- Abstract
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.
- Subjects
ASYMMETRIC synthesis; BRONSTED acids; ENANTIOSELECTIVE catalysis; HYDROGEN bonding; HYDROGENATION; RING formation (Chemistry)
- Publication
Angewandte Chemie, 2014, Vol 126, Issue 50, p13960
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201407677