Enantioselective nickel-catalyzed intramolecular allylic alkenylations enabled by reversible alkenylnickel E/Z isomerization
Enantioselective nickel-catalyzed arylative cyclizations of substrates containing a Z-allylic phosphate tethered to an alkyne are described. These reactions give multisubstituted chiral aza- and carbocycles, and are initiated by the addition of an arylboronic acid to the alkyne, followed by cyclizat...
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Wiley-VCH Verlag
2017
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| Online Access: | https://eprints.nottingham.ac.uk/43683/ |
| _version_ | 1848796743572914176 |
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| author | Yap, Connor Lenagh-Snow, Gabriel M.J. Narayan Karad, Somnath Lewis, William Diorazio, Louis J. Lam, Hon Wai |
| author_facet | Yap, Connor Lenagh-Snow, Gabriel M.J. Narayan Karad, Somnath Lewis, William Diorazio, Louis J. Lam, Hon Wai |
| author_sort | Yap, Connor |
| building | Nottingham Research Data Repository |
| collection | Online Access |
| description | Enantioselective nickel-catalyzed arylative cyclizations of substrates containing a Z-allylic phosphate tethered to an alkyne are described. These reactions give multisubstituted chiral aza- and carbocycles, and are initiated by the addition of an arylboronic acid to the alkyne, followed by cyclization of the resulting alkenylnickel species onto the allylic phosphate. The reversible E/Z isomerization of the alkenylnickel species is essential for the success of the reactions. |
| first_indexed | 2025-11-14T19:52:50Z |
| format | Article |
| id | nottingham-43683 |
| institution | University of Nottingham Malaysia Campus |
| institution_category | Local University |
| last_indexed | 2025-11-14T19:52:50Z |
| publishDate | 2017 |
| publisher | Wiley-VCH Verlag |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | nottingham-436832020-05-04T18:49:49Z https://eprints.nottingham.ac.uk/43683/ Enantioselective nickel-catalyzed intramolecular allylic alkenylations enabled by reversible alkenylnickel E/Z isomerization Yap, Connor Lenagh-Snow, Gabriel M.J. Narayan Karad, Somnath Lewis, William Diorazio, Louis J. Lam, Hon Wai Enantioselective nickel-catalyzed arylative cyclizations of substrates containing a Z-allylic phosphate tethered to an alkyne are described. These reactions give multisubstituted chiral aza- and carbocycles, and are initiated by the addition of an arylboronic acid to the alkyne, followed by cyclization of the resulting alkenylnickel species onto the allylic phosphate. The reversible E/Z isomerization of the alkenylnickel species is essential for the success of the reactions. Wiley-VCH Verlag 2017-06-12 Article PeerReviewed Yap, Connor, Lenagh-Snow, Gabriel M.J., Narayan Karad, Somnath, Lewis, William, Diorazio, Louis J. and Lam, Hon Wai (2017) Enantioselective nickel-catalyzed intramolecular allylic alkenylations enabled by reversible alkenylnickel E/Z isomerization. Angewandte Chemie International Edition, 56 . pp. 8216-8220. ISSN 1521-3773 Allylic substitution; Asymmetric catalysis; Cyclization; Isomerization; Nickel http://onlinelibrary.wiley.com/doi/10.1002/anie.201703380/abstract doi:10.1002/anie.201703380 doi:10.1002/anie.201703380 |
| spellingShingle | Allylic substitution; Asymmetric catalysis; Cyclization; Isomerization; Nickel Yap, Connor Lenagh-Snow, Gabriel M.J. Narayan Karad, Somnath Lewis, William Diorazio, Louis J. Lam, Hon Wai Enantioselective nickel-catalyzed intramolecular allylic alkenylations enabled by reversible alkenylnickel E/Z isomerization |
| title | Enantioselective nickel-catalyzed intramolecular allylic alkenylations enabled by reversible alkenylnickel E/Z isomerization |
| title_full | Enantioselective nickel-catalyzed intramolecular allylic alkenylations enabled by reversible alkenylnickel E/Z isomerization |
| title_fullStr | Enantioselective nickel-catalyzed intramolecular allylic alkenylations enabled by reversible alkenylnickel E/Z isomerization |
| title_full_unstemmed | Enantioselective nickel-catalyzed intramolecular allylic alkenylations enabled by reversible alkenylnickel E/Z isomerization |
| title_short | Enantioselective nickel-catalyzed intramolecular allylic alkenylations enabled by reversible alkenylnickel E/Z isomerization |
| title_sort | enantioselective nickel-catalyzed intramolecular allylic alkenylations enabled by reversible alkenylnickel e/z isomerization |
| topic | Allylic substitution; Asymmetric catalysis; Cyclization; Isomerization; Nickel |
| url | https://eprints.nottingham.ac.uk/43683/ https://eprints.nottingham.ac.uk/43683/ https://eprints.nottingham.ac.uk/43683/ |