Construction of Three Contiguous Tertiary Stereocenters from Aziridines in One Step

Construction of Three Contiguous Tertiary Stereocenters from Aziridines in One Step

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 meth...

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Veröffentlicht in:Organic letters 2007-11, Vol.9 (23), p.4677-4680
Hauptverfasser: Blyumin, Evgeniy V, Gallon, Helen J, Yudin, Andrei K
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creator Blyumin, Evgeniy V
Gallon, Helen J
Yudin, Andrei K
description 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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title Construction of Three Contiguous Tertiary Stereocenters from Aziridines in One Step
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