Journal of Organic Chemistry 2011-03-04

Ag(I)-catalyzed regioselective ring-opening of N-tosylaziridine and N-tosylazetidine with S-, O-, and N-nucleophiles and tethered dinucleophiles.

Milan Bera, Sanjay Pratihar, Sujit Roy

Index: J. Org. Chem. 76(5) , 1475-8, (2011)

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Abstract

[Ag(COD)(2)]PF(6) catalyzes the ring-opening of N-tosylaziridines and -azetidines with alcohols, amines, thiols, and related tethered 1,2-ethane dinucleophiles. Initial rate studies and DFT-based evaluation of stepwise energetics suggest an inverse relationship between the nucleophilic reactivity of a heteroatom donor and its binding affinity to cationic Ag(I).