Control of N-Heterocyclic Carbene Catalyzed Reactions of Enals: Asymmetric Synthesis of Oxindole-γ-Amino Acid Derivatives
Abstract
A strategy to control the switch between a non‐cycloaddition reaction and a cycloaddition reaction of enals, using N‐heterocyclic carbene (NHC) catalyisis, has been developed. The new scalable protocol leads to γ‐amino‐acid esters bearing a tetrasubstituted stereocenter in good yields and high stereoselectivities by homo‐Mannich reactions of enals and isatin‐derived ketimines. By simply changing the N‐ketimine substituent to an ortho‐hydroxy phenyl group, the corresponding spirocyclic oxindolo‐γ‐lactams are obtained.
Main Authors
Format
Articles
Research article
Published
2018
Series
Subjects
Publication in research information system
Publisher
Wiley-VCH.
The permanent address of the publication
https://urn.fi/URN:NBN:fi:jyu-201805222714Käytä tätä linkitykseen.
Review status
Peer reviewed
ISSN
1433-7851
DOI
https://doi.org/10.1002/anie.201708994
Language
English
Published in
Angewandte Chemie International Edition
Citation
- Chen, X.-Y., Xiong, J.-W., Liu, Q., Li, S., Sheng, H., von Essen, C., Rissanen, K., & Enders, D. (2018). Control of N-Heterocyclic Carbene Catalyzed Reactions of Enals: Asymmetric Synthesis of Oxindole-γ-Amino Acid Derivatives. Angewandte Chemie International Edition, 57(1), 300-304. https://doi.org/10.1002/anie.201708994
License
Copyright© 2018 Wiley-VCH Verlag GmbH &Co.