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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, Sven Mangelinckx UGent, Erika Leemans UGent, Bram Denolf and Norbert De Kimpe UGent (2010) ORGANIC & BIOMOLECULAR CHEMISTRY. 8(14). p.3251-3258
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
Please use this url to cite or link to this publication:
author
organization
year
type
journalArticle (original)
publication status
published
subject
keyword
AMINO CARBONYL-COMPOUNDS, THIOOXIME S-OXIDES, TERT-BUTANESULFINYL IMINES, STEREOCONTROLLED SYNTHESIS, HETEROCYCLIC CHEMISTRY, WEINREB AMIDES, SULFINIMINES, REAGENTS, ACIDS, DERIVATIVES
journal title
ORGANIC & BIOMOLECULAR CHEMISTRY
Org. Biomol. Chem.
volume
8
issue
14
pages
3251 - 3258
Web of Science type
Article
Web of Science id
000279566700020
JCR category
CHEMISTRY, ORGANIC
JCR impact factor
3.451 (2010)
JCR rank
12/56 (2010)
JCR quartile
1 (2010)
ISSN
1477-0520
DOI
10.1039/c001471k
language
English
UGent publication?
yes
classification
A1
copyright statement
I have transferred the copyright for this publication to the publisher
id
1004170
handle
http://hdl.handle.net/1854/LU-1004170
date created
2010-07-06 15:36:13
date last changed
2016-12-19 15:42:14
@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},
}

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.