Enantioselective synthesis of chiral cyclopent-2-enones by nickel-catalyzed desymmetrization of malonate esters
The enantioselective synthesis of highly functionalized chiral cyclopent-2-enones by the reaction of alkynyl malonate esters with arylboronic acids is described. These desymmetrizing arylative cyclizations are catalyzed by a chiral phosphinooxazoline–nickel complex, and cyclization is enabled by the...
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| Format: | Article |
| Language: | English |
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Wiley-VCH Verlag
2018
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| Online Access: | https://eprints.nottingham.ac.uk/53504/ |
| _version_ | 1848798950806519808 |
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| author | Karad, Somnath Narayan Panchal, Heena Clarke, Christopher Lewis, William Lam, Hon Wai |
| author_facet | Karad, Somnath Narayan Panchal, Heena Clarke, Christopher Lewis, William Lam, Hon Wai |
| author_sort | Karad, Somnath Narayan |
| building | Nottingham Research Data Repository |
| collection | Online Access |
| description | The enantioselective synthesis of highly functionalized chiral cyclopent-2-enones by the reaction of alkynyl malonate esters with arylboronic acids is described. These desymmetrizing arylative cyclizations are catalyzed by a chiral phosphinooxazoline–nickel complex, and cyclization is enabled by the reversible E/Z isomerization of alkenylnickel species. The general methodology is also applicable to the synthesis of 1,6-dihydropyridin-3(2H)- ones. |
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| format | Article |
| id | nottingham-53504 |
| institution | University of Nottingham Malaysia Campus |
| institution_category | Local University |
| language | English |
| last_indexed | 2025-11-14T20:27:55Z |
| publishDate | 2018 |
| publisher | Wiley-VCH Verlag |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | nottingham-535042019-06-19T04:30:24Z https://eprints.nottingham.ac.uk/53504/ Enantioselective synthesis of chiral cyclopent-2-enones by nickel-catalyzed desymmetrization of malonate esters Karad, Somnath Narayan Panchal, Heena Clarke, Christopher Lewis, William Lam, Hon Wai The enantioselective synthesis of highly functionalized chiral cyclopent-2-enones by the reaction of alkynyl malonate esters with arylboronic acids is described. These desymmetrizing arylative cyclizations are catalyzed by a chiral phosphinooxazoline–nickel complex, and cyclization is enabled by the reversible E/Z isomerization of alkenylnickel species. The general methodology is also applicable to the synthesis of 1,6-dihydropyridin-3(2H)- ones. Wiley-VCH Verlag 2018-07-16 Article PeerReviewed application/pdf en https://eprints.nottingham.ac.uk/53504/1/HWL%20Ni-desymmetrization%20of%20malonates%20ACIE%20manuscript.pdf Karad, Somnath Narayan, Panchal, Heena, Clarke, Christopher, Lewis, William and Lam, Hon Wai (2018) Enantioselective synthesis of chiral cyclopent-2-enones by nickel-catalyzed desymmetrization of malonate esters. Angewandte Chemie International Edition, 57 (29). pp. 9122-9125. ISSN 1433-7851 asymmetric catalysis; carbocycles; cyclization; isomerization; nickel https://onlinelibrary.wiley.com/doi/abs/10.1002/anie.201805578 doi:10.1002/anie.201805578 doi:10.1002/anie.201805578 |
| spellingShingle | asymmetric catalysis; carbocycles; cyclization; isomerization; nickel Karad, Somnath Narayan Panchal, Heena Clarke, Christopher Lewis, William Lam, Hon Wai Enantioselective synthesis of chiral cyclopent-2-enones by nickel-catalyzed desymmetrization of malonate esters |
| title | Enantioselective synthesis of chiral cyclopent-2-enones by nickel-catalyzed desymmetrization of malonate esters |
| title_full | Enantioselective synthesis of chiral cyclopent-2-enones by nickel-catalyzed desymmetrization of malonate esters |
| title_fullStr | Enantioselective synthesis of chiral cyclopent-2-enones by nickel-catalyzed desymmetrization of malonate esters |
| title_full_unstemmed | Enantioselective synthesis of chiral cyclopent-2-enones by nickel-catalyzed desymmetrization of malonate esters |
| title_short | Enantioselective synthesis of chiral cyclopent-2-enones by nickel-catalyzed desymmetrization of malonate esters |
| title_sort | enantioselective synthesis of chiral cyclopent-2-enones by nickel-catalyzed desymmetrization of malonate esters |
| topic | asymmetric catalysis; carbocycles; cyclization; isomerization; nickel |
| url | https://eprints.nottingham.ac.uk/53504/ https://eprints.nottingham.ac.uk/53504/ https://eprints.nottingham.ac.uk/53504/ |