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Asymmetric synthesis of new chiral N-sulfinyl 2,2-disubstituted aziridines by Grignard additions across alpha-chloro N-sulfinyl ketimines

Filip Colpaert (UGent) , Sven Mangelinckx (UGent) , Erika Leemans (UGent) , Bram Denolf and Norbert De Kimpe (UGent)
(2010) ORGANIC & BIOMOLECULAR CHEMISTRY. 8(14). p.3251-3258
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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

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Chicago
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.
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.
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.
MLA
Colpaert, Filip, Sven Mangelinckx, Erika Leemans, 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 8.14 (2010): 3251–3258. Print.
@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 ({\textrangle} 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},
  keyword      = {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://dx.doi.org/10.1039/c001471k},
  volume       = {8},
  year         = {2010},
}

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