Arylative intramolecular allylation of ketones with 1,3-enynes enabled by catalytic alkenyl-to-allyl 1,4-Rh(I) migration
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 product...
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| Format: | Article |
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Wiley-VCH Verlag
2017
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| Online Access: | https://eprints.nottingham.ac.uk/42584/ |
| _version_ | 1848796519502708736 |
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| author | Partridge, Benjamin M. Callingham, Michael Lewis, William Lam, Hon Wai |
| author_facet | Partridge, Benjamin M. Callingham, Michael Lewis, William Lam, Hon Wai |
| author_sort | Partridge, Benjamin M. |
| building | Nottingham Research Data Repository |
| collection | Online Access |
| description | 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. |
| first_indexed | 2025-11-14T19:49:16Z |
| format | Article |
| id | nottingham-42584 |
| institution | University of Nottingham Malaysia Campus |
| institution_category | Local University |
| last_indexed | 2025-11-14T19:49:16Z |
| publishDate | 2017 |
| publisher | Wiley-VCH Verlag |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | nottingham-425842020-05-04T18:49:45Z https://eprints.nottingham.ac.uk/42584/ 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 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. Wiley-VCH Verlag 2017-06-12 Article PeerReviewed Partridge, Benjamin M., Callingham, Michael, 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 http://onlinelibrary.wiley.com/doi/10.1002/anie.201703155/abstract;jsessionid=11B11CC2788E4CFE65F8314173C89D8C.f04t02 doi:10.1002/anie.201703155 doi:10.1002/anie.201703155 |
| spellingShingle | Partridge, Benjamin M. Callingham, Michael Lewis, William Lam, Hon Wai Arylative intramolecular allylation of ketones with 1,3-enynes enabled by catalytic alkenyl-to-allyl 1,4-Rh(I) migration |
| title | Arylative intramolecular allylation of ketones with 1,3-enynes enabled by catalytic alkenyl-to-allyl 1,4-Rh(I) migration |
| title_full | Arylative intramolecular allylation of ketones with 1,3-enynes enabled by catalytic alkenyl-to-allyl 1,4-Rh(I) migration |
| title_fullStr | Arylative intramolecular allylation of ketones with 1,3-enynes enabled by catalytic alkenyl-to-allyl 1,4-Rh(I) migration |
| title_full_unstemmed | Arylative intramolecular allylation of ketones with 1,3-enynes enabled by catalytic alkenyl-to-allyl 1,4-Rh(I) migration |
| title_short | Arylative intramolecular allylation of ketones with 1,3-enynes enabled by catalytic alkenyl-to-allyl 1,4-Rh(I) migration |
| title_sort | arylative intramolecular allylation of ketones with 1,3-enynes enabled by catalytic alkenyl-to-allyl 1,4-rh(i) migration |
| url | https://eprints.nottingham.ac.uk/42584/ https://eprints.nottingham.ac.uk/42584/ https://eprints.nottingham.ac.uk/42584/ |