Journal
ORGANIC LETTERS
Volume 10, Issue 20, Pages 4457-4460Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol801607r
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- Ministerio de Educacion y Cultura [CTQ2007-61132]
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An efficient and general synthesis of aziridines by the reaction of imines derived from p-toluenesulfonamides with in situ generated iodomethyllithium, with a simple and rapid experimental protocol, is reported for the first time. The reaction with the chiral aldimine derived from phenylalaninal allowed access to (2R,1'S)-2-(1'-aminoalkyl)aziridine with very high diastereoselectivity, in enantiopure form. A mechanism to explain this novel reaction is proposed.
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