Sigmatropic rearrangement of vinyl aziridines: expedient synthesis of cyclic sulfoximines from chiral sulfinimines
A novel rearrangement of 2-vinyl aziridine 2-carboxylates to unusual chiral cyclic sulfoximines is described herein. The method allows the synthesis of substituted cyclic sulfoximines in high yields with complete stereocontrol, displaying a wide substrate scope under mild conditions. Further develo...
| Main Authors: | , , , , , , , , , |
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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/42559/ |
| _version_ | 1848796514042773504 |
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| author | Moragas, Toni Liffey, Ryan M. Regentova, Dominika Ward, Jon-Paul Dutton, Justine Lewis, William Churcher, Ian Walton, Lesley Souto, J.A. Stockman, Robert A. |
| author_facet | Moragas, Toni Liffey, Ryan M. Regentova, Dominika Ward, Jon-Paul Dutton, Justine Lewis, William Churcher, Ian Walton, Lesley Souto, J.A. Stockman, Robert A. |
| author_sort | Moragas, Toni |
| building | Nottingham Research Data Repository |
| collection | Online Access |
| description | A novel rearrangement of 2-vinyl aziridine 2-carboxylates to unusual chiral cyclic sulfoximines is described herein. The method allows the synthesis of substituted cyclic sulfoximines in high yields with complete stereocontrol, displaying a wide substrate scope under mild conditions. Further development of a one-pot process directly from sulfinimines shows the synthetic applicability of this protocol, providing access to complex chiral sulfoximines in only two steps from commercially available aldehydes. A mechanistic hypothesis and synthetic application in the formal synthesis of trachelanthamidine by transformation of a cyclic sulfoximine into a pyrroline is also disclosed. |
| first_indexed | 2025-11-14T19:49:11Z |
| format | Article |
| id | nottingham-42559 |
| institution | University of Nottingham Malaysia Campus |
| institution_category | Local University |
| last_indexed | 2025-11-14T19:49:11Z |
| publishDate | 2016 |
| publisher | Wiley-VCH Verlag |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | nottingham-425592020-05-04T18:05:09Z https://eprints.nottingham.ac.uk/42559/ Sigmatropic rearrangement of vinyl aziridines: expedient synthesis of cyclic sulfoximines from chiral sulfinimines Moragas, Toni Liffey, Ryan M. Regentova, Dominika Ward, Jon-Paul Dutton, Justine Lewis, William Churcher, Ian Walton, Lesley Souto, J.A. Stockman, Robert A. A novel rearrangement of 2-vinyl aziridine 2-carboxylates to unusual chiral cyclic sulfoximines is described herein. The method allows the synthesis of substituted cyclic sulfoximines in high yields with complete stereocontrol, displaying a wide substrate scope under mild conditions. Further development of a one-pot process directly from sulfinimines shows the synthetic applicability of this protocol, providing access to complex chiral sulfoximines in only two steps from commercially available aldehydes. A mechanistic hypothesis and synthetic application in the formal synthesis of trachelanthamidine by transformation of a cyclic sulfoximine into a pyrroline is also disclosed. Wiley-VCH Verlag 2016-08-31 Article PeerReviewed Moragas, Toni, Liffey, Ryan M., Regentova, Dominika, Ward, Jon-Paul, Dutton, Justine, Lewis, William, Churcher, Ian, Walton, Lesley, Souto, J.A. and Stockman, Robert A. (2016) Sigmatropic rearrangement of vinyl aziridines: expedient synthesis of cyclic sulfoximines from chiral sulfinimines. Angewandte Chemie International Edition, 55 (34). pp. 10047-10051. ISSN 1521-3773 http://onlinelibrary.wiley.com/doi/10.1002/anie.201604188/abstract doi:10.1002/anie.201604188 doi:10.1002/anie.201604188 |
| spellingShingle | Moragas, Toni Liffey, Ryan M. Regentova, Dominika Ward, Jon-Paul Dutton, Justine Lewis, William Churcher, Ian Walton, Lesley Souto, J.A. Stockman, Robert A. Sigmatropic rearrangement of vinyl aziridines: expedient synthesis of cyclic sulfoximines from chiral sulfinimines |
| title | Sigmatropic rearrangement of vinyl aziridines: expedient synthesis of cyclic sulfoximines from chiral sulfinimines |
| title_full | Sigmatropic rearrangement of vinyl aziridines: expedient synthesis of cyclic sulfoximines from chiral sulfinimines |
| title_fullStr | Sigmatropic rearrangement of vinyl aziridines: expedient synthesis of cyclic sulfoximines from chiral sulfinimines |
| title_full_unstemmed | Sigmatropic rearrangement of vinyl aziridines: expedient synthesis of cyclic sulfoximines from chiral sulfinimines |
| title_short | Sigmatropic rearrangement of vinyl aziridines: expedient synthesis of cyclic sulfoximines from chiral sulfinimines |
| title_sort | sigmatropic rearrangement of vinyl aziridines: expedient synthesis of cyclic sulfoximines from chiral sulfinimines |
| url | https://eprints.nottingham.ac.uk/42559/ https://eprints.nottingham.ac.uk/42559/ https://eprints.nottingham.ac.uk/42559/ |