Journal
ORGANIC LETTERS
Volume 11, Issue 2, Pages 325-328Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol802487v
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Funding
- EPSRC [EP/C007999/1]
- Engineering and Physical Sciences Research Council [EP/C007999/1] Funding Source: researchfish
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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.
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