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Lithiation of N-Alkyl-(o-tolyl)aziridine: Stereoselective Synthesis of Isochromans

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journal contribution
posted on 2009-08-21, 00:00 authored by Mariangela Dammacco, Leonardo Degennaro, Saverio Florio, Renzo Luisi, Biagia Musio, Angela Altomare
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 2aj. The hydroxyalkylated derivatives 2dj were converted into important scaffolds such as isochromans 3ad. A stereoselective preparation of isochromans (R)-3b, (1R,3S)-3d, and (1R,3R)-3d has been developed starting from enantioenriched o-tolylaziridine.