Stereoselective synthesis of functionalized pyrrolidines by the diverted NH insertion reaction of metallocarbenes with β-aminoketone derivatives
A highly stereoselective route to functionalized pyrrolidines from the metal catalyzed diverted N-H insertion of a range of diazocarbonyl compounds with β-aminoketone derivatives is described. A number of catalysts (rhodium(II) carboxylate dimers, copper(I) triflate and an iron(III)porphyrin) are sh...
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| Format: | Article |
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Wiley-VCH Verlag
2016
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| Online Access: | https://eprints.nottingham.ac.uk/34962/ |
| _version_ | 1848794971718549504 |
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| author | Nicolle, Simon M. Lewis, William Hayes, Christopher J. Moody, Christopher J. |
| author_facet | Nicolle, Simon M. Lewis, William Hayes, Christopher J. Moody, Christopher J. |
| author_sort | Nicolle, Simon M. |
| building | Nottingham Research Data Repository |
| collection | Online Access |
| description | A highly stereoselective route to functionalized pyrrolidines from the metal catalyzed diverted N-H insertion of a range of diazocarbonyl compounds with β-aminoketone derivatives is described. A number of catalysts (rhodium(II) carboxylate dimers, copper(I) triflate and an iron(III)porphyrin) are shown to promote the process under mild conditions to give a wide range of highly substituted proline derivatives. The reaction starts with a metallocarbene N-H insertion but is diverted by an intermolecular aldol reaction. |
| first_indexed | 2025-11-14T19:24:40Z |
| format | Article |
| id | nottingham-34962 |
| institution | University of Nottingham Malaysia Campus |
| institution_category | Local University |
| last_indexed | 2025-11-14T19:24:40Z |
| publishDate | 2016 |
| publisher | Wiley-VCH Verlag |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | nottingham-349622020-05-04T17:42:40Z https://eprints.nottingham.ac.uk/34962/ Stereoselective synthesis of functionalized pyrrolidines by the diverted NH insertion reaction of metallocarbenes with β-aminoketone derivatives Nicolle, Simon M. Lewis, William Hayes, Christopher J. Moody, Christopher J. A highly stereoselective route to functionalized pyrrolidines from the metal catalyzed diverted N-H insertion of a range of diazocarbonyl compounds with β-aminoketone derivatives is described. A number of catalysts (rhodium(II) carboxylate dimers, copper(I) triflate and an iron(III)porphyrin) are shown to promote the process under mild conditions to give a wide range of highly substituted proline derivatives. The reaction starts with a metallocarbene N-H insertion but is diverted by an intermolecular aldol reaction. Wiley-VCH Verlag 2016-03-07 Article PeerReviewed Nicolle, Simon M., Lewis, William, Hayes, Christopher J. and Moody, Christopher J. (2016) Stereoselective synthesis of functionalized pyrrolidines by the diverted NH insertion reaction of metallocarbenes with β-aminoketone derivatives. Angewandte Chemie International Edition, 55 (11). pp. 3749-3753. ISSN 1433-7851 Aldol reaction; carbenes; diazo compounds; nitrogen heterocycles; transition-metal catalysis http://onlinelibrary.wiley.com/doi/10.1002/anie.201511433/abstract doi:10.1002/anie.201511433 doi:10.1002/anie.201511433 |
| spellingShingle | Aldol reaction; carbenes; diazo compounds; nitrogen heterocycles; transition-metal catalysis Nicolle, Simon M. Lewis, William Hayes, Christopher J. Moody, Christopher J. Stereoselective synthesis of functionalized pyrrolidines by the diverted NH insertion reaction of metallocarbenes with β-aminoketone derivatives |
| title | Stereoselective synthesis of functionalized pyrrolidines by the diverted NH insertion reaction of metallocarbenes with β-aminoketone derivatives |
| title_full | Stereoselective synthesis of functionalized pyrrolidines by the diverted NH insertion reaction of metallocarbenes with β-aminoketone derivatives |
| title_fullStr | Stereoselective synthesis of functionalized pyrrolidines by the diverted NH insertion reaction of metallocarbenes with β-aminoketone derivatives |
| title_full_unstemmed | Stereoselective synthesis of functionalized pyrrolidines by the diverted NH insertion reaction of metallocarbenes with β-aminoketone derivatives |
| title_short | Stereoselective synthesis of functionalized pyrrolidines by the diverted NH insertion reaction of metallocarbenes with β-aminoketone derivatives |
| title_sort | stereoselective synthesis of functionalized pyrrolidines by the diverted nh insertion reaction of metallocarbenes with β-aminoketone derivatives |
| topic | Aldol reaction; carbenes; diazo compounds; nitrogen heterocycles; transition-metal catalysis |
| url | https://eprints.nottingham.ac.uk/34962/ https://eprints.nottingham.ac.uk/34962/ https://eprints.nottingham.ac.uk/34962/ |