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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

Authors

Benjamin M. Partridge

Michael Callingham

William Lewis

HON LAM Hon.Lam@nottingham.ac.uk
Professor of Sustainable Chemistry



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 Mar 29, 2024
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

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