The authors acknowledge Degussa GmbH and the DFG (Schwerpunktprogramm Organokatalyse) for financial support as well the Fonds der Chemischen Industrie for a stipend given to B.J.N.
Asymmetric Brønsted Acid Catalysis: Enantioselective Nucleophilic Substitutions and 1,4-Additions†
Article first published online: 19 DEC 2007
Copyright © 2008 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 47, Issue 3, pages 593–596, January 4, 2008
How to Cite
Rueping, M., Nachtsheim, Boris J., Moreth, Stefan A. and Bolte, M. (2008), Asymmetric Brønsted Acid Catalysis: Enantioselective Nucleophilic Substitutions and 1,4-Additions. Angew. Chem. Int. Ed., 47: 593–596. doi: 10.1002/anie.200703668
- Issue published online: 21 DEC 2007
- Article first published online: 19 DEC 2007
- Manuscript Received: 10 AUG 2007
- Degussa GmbH
- Michael addition;
- nucleophilic substitution;
Executive decision: Depending on the catalyst (both N-triflylphosphoramides), the highly enantioselective Brønsted acid catalyzed addition of indoles to α,β-unsaturated carbonyl compounds provides either α-keto esters (up to 92 % ee, left side of the scheme), or a novel type of bisindole (right), which displays atropisomerism. The α-keto esters can also be converted into amino acids by a one-pot 1,4-addition-reductive amination reaction.