Synthesis of Optically Active Arylaziridines by Regio- and Stereospecific Lithiation of N-Bus-Phenylaziridine.

[摘要]：a,a-Disubstituted aziridines, e.g. I (R = SiMe2, D, SnBu3, Me, etc.), 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 a,a-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.

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