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

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: Feb 3, 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