Synthesis of optically active arylaziridines by regio- and stereospecific lithiation of N-Bus-phenylaziridine
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 1523-7060Full text not available from this repository.
Official URL: http://dx.doi.org/10.1021/ol802487v
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|
|Official Date:||15 January 2009|
|Number of Pages:||4|
|Page Range:||pp. 325-328|
|Access rights to Published version:||Restricted or Subscription Access|
|Funder:||Engineering and Physical Sciences Research Council (EPSRC)|
|Grant number:||EP/C007999/1 (EPSRC)|
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