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

详细信息    查看全文

• 作者：Biagia Musio ; Guy J. Clarkson ; Michael Shipman ; Saverio Florio ; Renzo Luisi
• 刊名：Organic Letters
• 出版年：2009
• 出版时间：January 15, 2009
• 年：2009
• 卷：11
• 期：2
• 页码：325-328
• 全文大小：177K
• 年卷期：v.11,no.2(January 15, 2009)
• ISSN：1523-7052

文摘

α,α-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 α,α-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.