Arylative Intramolecular Allylation of Ketones with 1,3-Enynes Enabled by Catalytic Alkenyl-to-Allyl 1,4-Rhodium(I) Migration

Angewandte Chemie
Benjamin M PartridgeHon Wai Lam

Abstract

Alkenyl-to-allyl 1,4-rhodium(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.

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Citations

Jan 23, 2018·Chemistry : a European Journal·Johnathon D Dooley, Hon Wai Lam
Sep 4, 2019·Chemical Communications : Chem Comm·Luke O'BrienHon Wai Lam
Dec 24, 2018·Chemical Communications : Chem Comm·Rebecca E RuscoeHon Wai Lam
Nov 8, 2019·The Journal of Organic Chemistry·Mohammed Anif PashaDhevalapally B Ramachary
Sep 11, 2020·Journal of the American Chemical Society·Marino BörjessonRuben Martin

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