Catalytic enantioselective arylative cyclizations of alkynyl 1,3-diketones by 1,4-rhodium(i) migration

Groves, Alistair; Sun, Jinwei; Parke, Hal R. I.; Callingham, Michael; Argent, Stephen P.; Taylor, Laurence J.; Lam, Hon Wai

Abstract

The enantioselective synthesis of densely functionalized polycarbocycles by the rhodium(I)-catalyzed reaction of arylboronic acids with 1,3-diketones is described. The key step in these desymmetrizing domino addition–cyclization reactions is an alkenyl-to-aryl 1,4-Rh(I) migration, which enables arylboronic acids to function effectively as 1,2-dimetalloarene surrogates.

Citation

Groves, A., Sun, J., Parke, H. R. I., Callingham, M., Argent, S. P., Taylor, L. J., & Lam, H. W. (2020). Catalytic enantioselective arylative cyclizations of alkynyl 1,3-diketones by 1,4-rhodium(i) migration. Chemical Science, 11(10), 2759–2764. https://doi.org/10.1039/c9sc06309a

• Journal Article Type: Article
• Acceptance Date: Feb 5, 2020
• Online Publication Date: Feb 6, 2020
• Publication Date: Mar 14, 2020
• Deposit Date: Mar 12, 2020
• Publicly Available Date: Mar 13, 2020
• Journal: Chemical Science
• Print ISSN: 2041-6520
• Electronic ISSN: 2041-6539
• Publisher: Royal Society of Chemistry
• Peer Reviewed: Peer Reviewed
• Volume: 11
• Issue: 10
• Pages: 2759–2764
• DOI: https://doi.org/10.1039/c9sc06309a
• Public URL: https://nottingham-repository.worktribe.com/output/3970952
• Publisher URL: https://pubs.rsc.org/en/content/articlelanding/2020/SC/C9SC06309A#!divAbstract
• Additional Information: : This document is Similarity Check deposited; : Supplementary Information; : Crystal Structure Data; : Stephen P. Argent (ResearcherID); : Hon Wai Lam (ORCID); : Single-blind; : Received 12 December 2019; Accepted 5 February 2020; Accepted Manuscript published 6 February 2020; Advance Article published 11 February 2020