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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. doi:10.1021/ol802487v 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 | ||||
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Subjects: | Q Science > QD Chemistry | ||||
Divisions: | Faculty of Science, Engineering and Medicine > Science > Chemistry | ||||
Journal or Publication Title: | Organic Letters | ||||
Publisher: | American Chemical Society | ||||
ISSN: | 1523-7060 | ||||
Official Date: | 15 January 2009 | ||||
Dates: |
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Volume: | Vol.11 | ||||
Number: | No.2 | ||||
Number of Pages: | 4 | ||||
Page Range: | pp. 325-328 | ||||
DOI: | 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) |
Data sourced from Thomson Reuters' Web of Knowledge
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