Asymmetric synthesis of new chiral N-sulfinyl 2,2-disubstituted aziridines by Grignard additions across alpha-chloro N-sulfinyl ketimines
- Author
- Filip Colpaert (UGent) , Sven Mangelinckx (UGent) , Erika Leemans (UGent) , Bram Denolf and Norbert De Kimpe (UGent)
- Organization
- Abstract
- Reaction of chiral alpha-chloro N-tert-butanesulfinyl ketimines with Grignard reagents afforded new chiral N-sulfinyl 2,2-disubstituted aziridines in good to excellent diastereomeric ratio (dr up to 98:2). The 1,2,2-trisubstituted aziridines were isolated in high overall yield (51-85%) and with excellent enantiomeric excess (> 98% ee). The stereoselectivity obtained in the Grignard addition is rationalized by the coordinating ability of the alpha-chloro atom resulting in the opposite stereochemical outcome as observed for nonfunctionalized N-sulfinyl ketimines
- Keywords
- AMINO CARBONYL-COMPOUNDS, THIOOXIME S-OXIDES, TERT-BUTANESULFINYL IMINES, STEREOCONTROLLED SYNTHESIS, HETEROCYCLIC CHEMISTRY, WEINREB AMIDES, SULFINIMINES, REAGENTS, ACIDS, DERIVATIVES
Downloads
-
(...).pdf
- full text
- |
- UGent only
- |
- |
- 229.37 KB
Citation
Please use this url to cite or link to this publication: http://hdl.handle.net/1854/LU-1004170
- MLA
- Colpaert, Filip, et al. “Asymmetric Synthesis of New Chiral N-Sulfinyl 2,2-Disubstituted Aziridines by Grignard Additions across Alpha-Chloro N-Sulfinyl Ketimines.” ORGANIC & BIOMOLECULAR CHEMISTRY, vol. 8, no. 14, 2010, pp. 3251–58, doi:10.1039/c001471k.
- APA
- Colpaert, F., Mangelinckx, S., Leemans, E., Denolf, B., & De Kimpe, N. (2010). Asymmetric synthesis of new chiral N-sulfinyl 2,2-disubstituted aziridines by Grignard additions across alpha-chloro N-sulfinyl ketimines. ORGANIC & BIOMOLECULAR CHEMISTRY, 8(14), 3251–3258. https://doi.org/10.1039/c001471k
- Chicago author-date
- Colpaert, Filip, Sven Mangelinckx, Erika Leemans, Bram Denolf, and Norbert De Kimpe. 2010. “Asymmetric Synthesis of New Chiral N-Sulfinyl 2,2-Disubstituted Aziridines by Grignard Additions across Alpha-Chloro N-Sulfinyl Ketimines.” ORGANIC & BIOMOLECULAR CHEMISTRY 8 (14): 3251–58. https://doi.org/10.1039/c001471k.
- Chicago author-date (all authors)
- Colpaert, Filip, Sven Mangelinckx, Erika Leemans, Bram Denolf, and Norbert De Kimpe. 2010. “Asymmetric Synthesis of New Chiral N-Sulfinyl 2,2-Disubstituted Aziridines by Grignard Additions across Alpha-Chloro N-Sulfinyl Ketimines.” ORGANIC & BIOMOLECULAR CHEMISTRY 8 (14): 3251–3258. doi:10.1039/c001471k.
- Vancouver
- 1.Colpaert F, Mangelinckx S, Leemans E, Denolf B, De Kimpe N. Asymmetric synthesis of new chiral N-sulfinyl 2,2-disubstituted aziridines by Grignard additions across alpha-chloro N-sulfinyl ketimines. ORGANIC & BIOMOLECULAR CHEMISTRY. 2010;8(14):3251–8.
- IEEE
- [1]F. Colpaert, S. Mangelinckx, E. Leemans, B. Denolf, and N. De Kimpe, “Asymmetric synthesis of new chiral N-sulfinyl 2,2-disubstituted aziridines by Grignard additions across alpha-chloro N-sulfinyl ketimines,” ORGANIC & BIOMOLECULAR CHEMISTRY, vol. 8, no. 14, pp. 3251–3258, 2010.
@article{1004170,
abstract = {{Reaction of chiral alpha-chloro N-tert-butanesulfinyl ketimines with Grignard reagents afforded new chiral N-sulfinyl 2,2-disubstituted aziridines in good to excellent diastereomeric ratio (dr up to 98:2). The 1,2,2-trisubstituted aziridines were isolated in high overall yield (51-85%) and with excellent enantiomeric excess (> 98% ee). The stereoselectivity obtained in the Grignard addition is rationalized by the coordinating ability of the alpha-chloro atom resulting in the opposite stereochemical outcome as observed for nonfunctionalized N-sulfinyl ketimines}},
author = {{Colpaert, Filip and Mangelinckx, Sven and Leemans, Erika and Denolf, Bram and De Kimpe, Norbert}},
issn = {{1477-0520}},
journal = {{ORGANIC & BIOMOLECULAR CHEMISTRY}},
keywords = {{AMINO CARBONYL-COMPOUNDS,THIOOXIME S-OXIDES,TERT-BUTANESULFINYL IMINES,STEREOCONTROLLED SYNTHESIS,HETEROCYCLIC CHEMISTRY,WEINREB AMIDES,SULFINIMINES,REAGENTS,ACIDS,DERIVATIVES}},
language = {{eng}},
number = {{14}},
pages = {{3251--3258}},
title = {{Asymmetric synthesis of new chiral N-sulfinyl 2,2-disubstituted aziridines by Grignard additions across alpha-chloro N-sulfinyl ketimines}},
url = {{http://doi.org/10.1039/c001471k}},
volume = {{8}},
year = {{2010}},
}
- Altmetric
- View in Altmetric
- Web of Science
- Times cited: