(Chemical Equation Presented) The lithiation reaction of o-tolylaziridine 1 has been investigated by using the aziridine ring capability to act as a directing metalation group. Trapped with electrophiles, the resulting o-aziridinyl benzyllithium 1-Li gives access to several functionalized aziridines 2a-j. The hydroxyalkylated derivatives 2d-j were converted into important scaffolds such as isochromans 3a-d. A stereoselective preparation of isochromans (R)-3b, (1R,3S)-3d, and (1R,3R)-3d has been developed starting from enantioenriched o-tolylaziridine. © 2009 American Chemical Society.
Lithiation of N-alkyl-(o-tolyl)aziridine: Stereoselective synthesis of isochromans / Dammacco, M.; Degennaro, L.; Florio, S.; Luisi, R.; Musio, B.; Altomare, A.. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - 74:16(2009), pp. 6319-6322. [10.1021/jo9011943]
Lithiation of N-alkyl-(o-tolyl)aziridine: Stereoselective synthesis of isochromans
Dammacco M.;Musio B.;
2009
Abstract
(Chemical Equation Presented) The lithiation reaction of o-tolylaziridine 1 has been investigated by using the aziridine ring capability to act as a directing metalation group. Trapped with electrophiles, the resulting o-aziridinyl benzyllithium 1-Li gives access to several functionalized aziridines 2a-j. The hydroxyalkylated derivatives 2d-j were converted into important scaffolds such as isochromans 3a-d. A stereoselective preparation of isochromans (R)-3b, (1R,3S)-3d, and (1R,3R)-3d has been developed starting from enantioenriched o-tolylaziridine. © 2009 American Chemical Society.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
