Enantioselective nickel-catalyzed arylative intramolecular allylations of allenyl electrophiles
Catalytic enantioselective conjugate additions of organometallic reagents to electron-deficient alkenes and asymmetric allylation of carbonyl compounds are important reactions for the construction of new carbon-carbon bonds. However, a method using an allylnickel species to perform catalytic nucleop...
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| Format: | Thesis (University of Nottingham only) |
| Language: | English |
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2020
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| Online Access: | https://eprints.nottingham.ac.uk/59765/ |
| _version_ | 1848799671263166464 |
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| author | NGUYEN, THI LE NHON |
| author_facet | NGUYEN, THI LE NHON |
| author_sort | NGUYEN, THI LE NHON |
| building | Nottingham Research Data Repository |
| collection | Online Access |
| description | Catalytic enantioselective conjugate additions of organometallic reagents to electron-deficient alkenes and asymmetric allylation of carbonyl compounds are important reactions for the construction of new carbon-carbon bonds. However, a method using an allylnickel species to perform catalytic nucleophilic allylation enantioselectively remains considerably underdeveloped and only a handful of examples have been described. In this thesis, enantioselective nickel-catalyzed arylative and alkenylative intramolecular allylations of allenyl electrophiles with boronic acids are described.
Enantioselective nickel-catalyzed arylative intramolecular 1,4-allylations
An asymmetric nickel-catalyzed desymmetrization of allenyl cyclohexa-2,5-dienones by reaction with arylboronic acids is reported. In this study, nucleophilic allylnickel species, formed by nickel-catalyzed arylation of the allene, undergo 1,4-allylation-cyclization reaction to furnish hexahydroindol-5-ones and hexahydrobenzofuran-5-ones with three contiguous stereocenters in high diastereo- and enantioselectivities (87−99% ee).
Enantioselective nickel-catalyzed arylative and alkenylative intramolecular 1,2-allylations
An asymmetric nickel-catalyzed cascade reaction of allenyl ketones with boronic acids is described. In this project, a nickel-catalyzed arylation and alkenylation of the allene gives allylnickel species, which undergo a 1,2-allylation-cyclization with tethered ketones to furnish 3-hydroxypyrrolidin-2-ones, 3-hydroxypyrrolidines and 4-hydroxypiperidines in high diastereo- and enantioselectivities. |
| first_indexed | 2025-11-14T20:39:22Z |
| format | Thesis (University of Nottingham only) |
| id | nottingham-59765 |
| institution | University of Nottingham Malaysia Campus |
| institution_category | Local University |
| language | English |
| last_indexed | 2025-11-14T20:39:22Z |
| publishDate | 2020 |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | nottingham-597652025-02-28T14:45:48Z https://eprints.nottingham.ac.uk/59765/ Enantioselective nickel-catalyzed arylative intramolecular allylations of allenyl electrophiles NGUYEN, THI LE NHON Catalytic enantioselective conjugate additions of organometallic reagents to electron-deficient alkenes and asymmetric allylation of carbonyl compounds are important reactions for the construction of new carbon-carbon bonds. However, a method using an allylnickel species to perform catalytic nucleophilic allylation enantioselectively remains considerably underdeveloped and only a handful of examples have been described. In this thesis, enantioselective nickel-catalyzed arylative and alkenylative intramolecular allylations of allenyl electrophiles with boronic acids are described. Enantioselective nickel-catalyzed arylative intramolecular 1,4-allylations An asymmetric nickel-catalyzed desymmetrization of allenyl cyclohexa-2,5-dienones by reaction with arylboronic acids is reported. In this study, nucleophilic allylnickel species, formed by nickel-catalyzed arylation of the allene, undergo 1,4-allylation-cyclization reaction to furnish hexahydroindol-5-ones and hexahydrobenzofuran-5-ones with three contiguous stereocenters in high diastereo- and enantioselectivities (87−99% ee). Enantioselective nickel-catalyzed arylative and alkenylative intramolecular 1,2-allylations An asymmetric nickel-catalyzed cascade reaction of allenyl ketones with boronic acids is described. In this project, a nickel-catalyzed arylation and alkenylation of the allene gives allylnickel species, which undergo a 1,2-allylation-cyclization with tethered ketones to furnish 3-hydroxypyrrolidin-2-ones, 3-hydroxypyrrolidines and 4-hydroxypiperidines in high diastereo- and enantioselectivities. 2020-07-15 Thesis (University of Nottingham only) NonPeerReviewed application/pdf en arr https://eprints.nottingham.ac.uk/59765/1/TLN_Nguyen_Corrected%20Thesis.pdf NGUYEN, THI LE NHON (2020) Enantioselective nickel-catalyzed arylative intramolecular allylations of allenyl electrophiles. PhD thesis, University of Nottingham. Asymmetric catalysis Allylation Arylation Cyclization Nickel |
| spellingShingle | Asymmetric catalysis Allylation Arylation Cyclization Nickel NGUYEN, THI LE NHON Enantioselective nickel-catalyzed arylative intramolecular allylations of allenyl electrophiles |
| title | Enantioselective nickel-catalyzed arylative intramolecular allylations of allenyl electrophiles |
| title_full | Enantioselective nickel-catalyzed arylative intramolecular allylations of allenyl electrophiles |
| title_fullStr | Enantioselective nickel-catalyzed arylative intramolecular allylations of allenyl electrophiles |
| title_full_unstemmed | Enantioselective nickel-catalyzed arylative intramolecular allylations of allenyl electrophiles |
| title_short | Enantioselective nickel-catalyzed arylative intramolecular allylations of allenyl electrophiles |
| title_sort | enantioselective nickel-catalyzed arylative intramolecular allylations of allenyl electrophiles |
| topic | Asymmetric catalysis Allylation Arylation Cyclization Nickel |
| url | https://eprints.nottingham.ac.uk/59765/ |