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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 Wai Lam



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.

Journal Article Type Article
Publication Date Jun 12, 2017
Journal Angewandte Chemie International Edition
Print ISSN 1433-7851
Electronic ISSN 1521-3773
Publisher Wiley
Peer Reviewed Peer Reviewed
Volume 56
Issue 25
APA6 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
DOI https://doi.org/10.1002/anie.201703155
Publisher URL http://onlinelibrary.wiley.com/doi/10.1002/anie.201703155/abstract;jsessionid=11B11CC2788E4CFE65F8314173C89D8C.f04t02
Copyright Statement Copyright information regarding this work can be found at the following address: http://creativecommons.org/licenses/by/4.0

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Copyright Statement
Copyright information regarding this work can be found at the following address: http://creativecommons.org/licenses/by/4.0





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