Rh(I)-Catalyzed Regio- and Enantioselective Ring Opening of Vinyl Cyclopropanes

Journal article

We describe a Rh­(I) catalyzed asymmetric ring opening of racemic vinyl cyclopropanes using aryl boronic acids as C-nucleophiles. When ferrocene-based chiral bisphosphines are used as ligands, the products are obtained with regioselectivities typically 99:1 r.r. and ee’s generally between 88 and 96%. A wide range of aryl boronic acids can be used, and the products can be converted into a variety of targets. Preliminary mechanistic studies indicate that Zn­(OTf)2 plays a significant role in the reaction by promoting rhodium-ligand complex formation and accelerating the reaction. We expect this method and these mechanistic insights to be useful in the development of new asymmetric methods.

Authors: Webster, SJ; Balázs, LB; Goetzke, FW; Stojalnikova, V; Liu, K

• Publication status: Published
• Peer review status: Peer reviewed
• Publisher: American Chemical Society
• Journal: Journal of the American Chemical Society
• Volume: 146
• Issue: 35
• Pages: 24708-24715
• Publication date: 2024-08-20
• Acceptance date: 2024-08-08
• DOI: 10.1021/jacs.4c09490
• EISSN: 1520-5126
• ISSN: 0002-7863
• Language: English