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Synthesis of optically active arylaziridines by regio- and stereospecific lithiation of N-Bus-phenylaziridine
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Musio, Biagia, Clarkson, Guy J., Shipman, Michael, Florio, Saverio and Luisi, Renzo. (2009) Synthesis of optically active arylaziridines by regio- and stereospecific lithiation of N-Bus-phenylaziridine. Organic Letters, Vol.11 (No.2). pp. 325-328. ISSN 1523-7060
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Official URL: http://dx.doi.org/10.1021/ol802487v
Abstract
alpha,alpha-Disubstituted aziridines can be produced in good yields by selective lithiation of N-tert-butylsulfonyl-2-phenylaziridine (n-BuLi/TMEDA, Et2O) at the benzylic position and subsequent trapping with a range of electrophiles. Repetition of the lithiation/electrophilic trapping sequence provides a stereocontrolled route to trisubstituted aziridines. Using (R)-N-tert-butylsulfonyl-2-phenylaziridine, the alpha,alpha-disubstituted aziridines can be produced as single enantiomers (er >98:2), indicating that the intermediate organolithium is configurationally stable. Efficient aziridine ring-opening reactions leading to 1,2-diamines and 1,4-diamines are also reported.
| Item Type: | Journal Article |
|---|---|
| Subjects: | Q Science > QD Chemistry |
| Divisions: | Faculty of Science > Chemistry |
| Journal or Publication Title: | Organic Letters |
| Publisher: | American Chemical Society |
| ISSN: | 1523-7060 |
| Date: | 15 January 2009 |
| Volume: | Vol.11 |
| Number: | No.2 |
| Number of Pages: | 4 |
| Page Range: | pp. 325-328 |
| Identification Number: | 10.1021/ol802487v |
| Status: | Peer Reviewed |
| Publication Status: | Published |
| Access rights to Published version: | Restricted or Subscription Access |
| Funder: | Engineering and Physical Sciences Research Council (EPSRC) |
| Grant number: | EP/C007999/1 (EPSRC) |
| URI: | http://wrap.warwick.ac.uk/id/eprint/28703 |
Data sourced from Thomson Reuters' Web of Knowledge
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