Regio- and stereoselective lithiation and electrophilic substitution reactions of N-Alkyl-2,3-diphenylaziridines: solvent effect.
[structure: see text]. The lithiation reaction of cis- and trans-N-alkyl-2,3-diphenylaziridines has been investigated. While cis-diphenylaziridines do not undergo any lithiation upon treatment with organolithiums, the lithiation reaction of the trans counterparts is completely alpha-regioselective and the stereochemical course of the lithiation-trapping sequence is solvent dependent: inversion of configuration in coordinating solvents (THF or toluene/crown ether) and retention in hexane, ether, or toluene. The preparation of stereodefined functionalized N-alkyl-2,3-diphenylaziridines is described.
Luisi
Renzo
R
Dipartimento Farmaco-Chimico, Università di Bari, CNR, Istituto di Chimica dei Composti OrganoMetallici ICCOM, Sezione di Bari, Via E Orabona 4, I-70125 Bari, Italy.
Capriati
Vito
V
Florio
Saverio
S
Musio
Biagia
B
D001388:Aziridines / Q000737:chemistry*; D004563:Electrochemistry; D008094:Lithium / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D012997:Solvents / Q000737:chemistry*; D013237:Stereoisomerism
D001388:Aziridines; D009942:Organometallic Compounds; D012997:Solvents; D008094:Lithium