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Construction of Three Contiguous Tertiary Stereocenters from Aziridines in One Step

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journal contribution
posted on 08.11.2007, 00:00 by Evgeniy V. Blyumin, Helen J. Gallon, Andrei K. Yudin
A range of active methylene nucleophiles were found to participate in ring-opening of tosylated aziridines under mild phase-transfer catalyzed conditions. High isolated yields coupled with a 1:1 reaction stoichiometry and high levels of relative stereocontrol are distinguishing features of this method. The products are obtained without epimerization, underscoring the optimal conditions afforded by the phase-transfer catalysis for connecting active methylene nucleophiles and weakly electrophilic N-tosylated aziridines.

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