Synthesis of optically active arylaziridines by regio- and stereospecific lithiation of N-bus-phenylaziridine.
Alpha,alpha-disubstituted aziridines can be produced in good yields by selective lithiation of N-tert-butylsulfonyl-2-phenylaziridine (n-BuLi/TMEDA, Et(2)O) 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.
Musio
Biagia
B
Department of Chemistry, University of Warwick, Gibbet Hill Road, Coventry CV4 7AL, UK.
Clarkson
Guy J
GJ
Shipman
Michael
M
Florio
Saverio
S
Luisi
Renzo
R
D001388:Aziridines / Q000138:chemical synthesis* / Q000737:chemistry; D008094:Lithium / Q000737:chemistry*; D009904:Optical Rotation; D013237:Stereoisomerism; D013379:Substrate Specificity
D001388:Aziridines; C033132:aziridine; D008094:Lithium