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

Partridge, Benjamin M. and Callingham, Michael and Lewis, William and Lam, Hon Wai (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). pp. 7227-7232. ISSN 1521-3773

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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.

Item Type: Article
Schools/Departments: University of Nottingham, UK > Faculty of Science > School of Chemistry
Identification Number: 10.1002/anie.201703155
Depositing User: Eprints, Support
Date Deposited: 08 May 2017 12:22
Last Modified: 08 Jun 2017 07:30
URI: http://eprints.nottingham.ac.uk/id/eprint/42584

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