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 α-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. © 2007 American Chemical Society.
Regio- and stereoselective lithiation and electrophilic substitution reactions of N-alkyl-2,3-diphenylaziridines: Solvent effect / Luisi, R.; Capriati, V.; Florio, S.; Musio, B.. - In: ORGANIC LETTERS. - ISSN 1523-7060. - 9:7(2007), pp. 1263-1266. [10.1021/ol0700714]
Regio- and stereoselective lithiation and electrophilic substitution reactions of N-alkyl-2,3-diphenylaziridines: Solvent effect
Musio B.
2007
Abstract
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 α-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. © 2007 American Chemical Society.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
