Arylative intramolecular allylation of ketones with 1,3-enynes enabled by catalytic alkenyl-to-allyl 1,4-Rh(I) migration

Partridge, Benjamin M.; Callingham, Michael; Lewis, William; Lam, Hon Wai

Abstract

Alkenyl-to-allyl 1,4-Rh(I) migration enables the generation of nucleophilic allylrhodium(I) species by remote C–H activation. This new mode of reactivity was employed in the diastereoselective reaction of arylboron reagents with substrates containing a 1,3-enyne tethered to a ketone, to give products containing three contiguous stereocenters. The products can be obtained in high enantioselectivities using a chiral sulfur–alkene ligand.

Citation

Partridge, B. . M., Callingham, M., Lewis, W., & Lam, H. W. (2017). Arylative intramolecular allylation of ketones with 1,3-enynes enabled by catalytic alkenyl-to-allyl 1,4-Rh(I) migration. Angewandte Chemie International Edition, 56(25), https://doi.org/10.1002/anie.201703155

• Journal Article Type: Article
• Acceptance Date: Apr 26, 2017
• Online Publication Date: May 19, 2017
• Publication Date: Jun 12, 2017
• Deposit Date: May 8, 2017
• Publicly Available Date: May 19, 2017
• Journal: Angewandte Chemie International Edition
• Print ISSN: 1433-7851
• Electronic ISSN: 1521-3773
• Publisher: Wiley
• Peer Reviewed: Peer Reviewed
• Volume: 56
• Issue: 25
• DOI: https://doi.org/10.1002/anie.201703155
• Public URL: https://nottingham-repository.worktribe.com/output/865599
• Publisher URL: http://onlinelibrary.wiley.com/doi/10.1002/anie.201703155/abstract;jsessionid=11B11CC2788E4CFE65F8314173C89D8C.f04t02
• Contract Date: May 8, 2017