Raja Rit
A Scalable Synthesis of Chiral Himbert Diene Ligands for Asymmetric Catalysis
Rit, Raja; Li, Hongyi; Argent, Stephen P.; Wheelhouse, Katherine M.; Woodward, Simon; Lam, Hon Wai
Authors
Hongyi Li
STEPHEN ARGENT stephen.argent@nottingham.ac.uk
Senior Research Fellow
Katherine M. Wheelhouse
SIMON WOODWARD simon.woodward@nottingham.ac.uk
Professor of Synthetic Organic Chemistry
HON LAM Hon.Lam@nottingham.ac.uk
Professor of Sustainable Chemistry
Abstract
Chiral dienes are important ligands in asymmetric catalysis but they are less accessible than other commonly used ligands such as chiral bisphosphines. Here, we show that intramolecular [4 + 2] cycloaddition of a simply attained chiral allenecarboxanilide readily affords pseudoenantiomeric bicyclo[2.2.2]octa-2,5-dienes containing an alkenyl bromide, which can be readily functionalized to give diverse chiral diene ligands. The synthesis is straightforward and easily conducted on multigram scales. These ligands exhibit high performance in nine types of enantioselective Rh(I)-catalyzed 1,4-addition or 1,2-addition reactions.
Citation
Rit, R., Li, H., Argent, S. P., Wheelhouse, K. M., Woodward, S., & Lam, H. W. (2023). A Scalable Synthesis of Chiral Himbert Diene Ligands for Asymmetric Catalysis. Advanced Synthesis and Catalysis, 365(10), 1629-1639. https://doi.org/10.1002/adsc.202300039
Journal Article Type | Article |
---|---|
Acceptance Date | Jan 24, 2023 |
Online Publication Date | Jan 24, 2023 |
Publication Date | May 23, 2023 |
Deposit Date | Jan 26, 2023 |
Publicly Available Date | Feb 3, 2023 |
Journal | Advanced Synthesis and Catalysis |
Print ISSN | 1615-4150 |
Electronic ISSN | 1615-4169 |
Publisher | Wiley |
Peer Reviewed | Peer Reviewed |
Volume | 365 |
Issue | 10 |
Pages | 1629-1639 |
DOI | https://doi.org/10.1002/adsc.202300039 |
Keywords | General Chemistry |
Public URL | https://nottingham-repository.worktribe.com/output/16503043 |
Publisher URL | https://onlinelibrary.wiley.com/doi/10.1002/adsc.202300039 |
Files
Adv Synth Catal - 2023 - Rit - A Scalable Synthesis of Chiral Himbert Diene Ligands for Asymmetric Catalysis
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Publisher Licence URL
https://creativecommons.org/licenses/by/4.0/
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