Asymmetric synthesis of pyrrolidine-containing chemical scaffolds via Tsuji-Trost allylation of N-tert-butanesulfinyl imines
A simple and efficient asymmetric synthesis of novel sp3 rich pyrrolidine chemical scaffolds over five steps starting from simple ketones is described. Key steps involve the use of tert-butanesulfinamide as a chiral auxiliary to perform an asymmetric Tsuji-Trost allylation, with subsequent cross-met...
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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/46526/ |
| _version_ | 1848797347814834176 |
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| author | Dawood, Rafid S. Georgiou, Irene Wilkie, Ross P. Lewis, William Stockman, Robert A. |
| author_facet | Dawood, Rafid S. Georgiou, Irene Wilkie, Ross P. Lewis, William Stockman, Robert A. |
| author_sort | Dawood, Rafid S. |
| building | Nottingham Research Data Repository |
| collection | Online Access |
| description | A simple and efficient asymmetric synthesis of novel sp3 rich pyrrolidine chemical scaffolds over five steps starting from simple ketones is described. Key steps involve the use of tert-butanesulfinamide as a chiral auxiliary to perform an asymmetric Tsuji-Trost allylation, with subsequent cross-metathesis with an acrylate ester and reduction of the sulfinimine/cyclisation of the resulting amine giving the pyrrolidine scaffolds in high yields and diastereoselectivites. By removing the chiral auxiliary and functionalising the ester group, the resulting scaffold core can be further derivatised. |
| first_indexed | 2025-11-14T20:02:26Z |
| format | Article |
| id | nottingham-46526 |
| institution | University of Nottingham Malaysia Campus |
| institution_category | Local University |
| last_indexed | 2025-11-14T20:02:26Z |
| publishDate | 2017 |
| publisher | Wiley-VCH Verlag |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | nottingham-465262020-05-04T19:00:41Z https://eprints.nottingham.ac.uk/46526/ Asymmetric synthesis of pyrrolidine-containing chemical scaffolds via Tsuji-Trost allylation of N-tert-butanesulfinyl imines Dawood, Rafid S. Georgiou, Irene Wilkie, Ross P. Lewis, William Stockman, Robert A. A simple and efficient asymmetric synthesis of novel sp3 rich pyrrolidine chemical scaffolds over five steps starting from simple ketones is described. Key steps involve the use of tert-butanesulfinamide as a chiral auxiliary to perform an asymmetric Tsuji-Trost allylation, with subsequent cross-metathesis with an acrylate ester and reduction of the sulfinimine/cyclisation of the resulting amine giving the pyrrolidine scaffolds in high yields and diastereoselectivites. By removing the chiral auxiliary and functionalising the ester group, the resulting scaffold core can be further derivatised. Wiley-VCH Verlag 2017-08-16 Article PeerReviewed Dawood, Rafid S., Georgiou, Irene, Wilkie, Ross P., Lewis, William and Stockman, Robert A. (2017) Asymmetric synthesis of pyrrolidine-containing chemical scaffolds via Tsuji-Trost allylation of N-tert-butanesulfinyl imines. Chemistry - a European Journal, 23 (46). pp. 11153-11158. ISSN 1521-3765 http://onlinelibrary.wiley.com/doi/10.1002/chem.201702616/abstract doi:10.1002/chem.201702616 doi:10.1002/chem.201702616 |
| spellingShingle | Dawood, Rafid S. Georgiou, Irene Wilkie, Ross P. Lewis, William Stockman, Robert A. Asymmetric synthesis of pyrrolidine-containing chemical scaffolds via Tsuji-Trost allylation of N-tert-butanesulfinyl imines |
| title | Asymmetric synthesis of pyrrolidine-containing chemical scaffolds via Tsuji-Trost allylation of N-tert-butanesulfinyl imines |
| title_full | Asymmetric synthesis of pyrrolidine-containing chemical scaffolds via Tsuji-Trost allylation of N-tert-butanesulfinyl imines |
| title_fullStr | Asymmetric synthesis of pyrrolidine-containing chemical scaffolds via Tsuji-Trost allylation of N-tert-butanesulfinyl imines |
| title_full_unstemmed | Asymmetric synthesis of pyrrolidine-containing chemical scaffolds via Tsuji-Trost allylation of N-tert-butanesulfinyl imines |
| title_short | Asymmetric synthesis of pyrrolidine-containing chemical scaffolds via Tsuji-Trost allylation of N-tert-butanesulfinyl imines |
| title_sort | asymmetric synthesis of pyrrolidine-containing chemical scaffolds via tsuji-trost allylation of n-tert-butanesulfinyl imines |
| url | https://eprints.nottingham.ac.uk/46526/ https://eprints.nottingham.ac.uk/46526/ https://eprints.nottingham.ac.uk/46526/ |