Organic Letters 2011-08-19

Access to optically active 3-azido- and 3-aminopiperidine derivatives by enantioselective ring expansion of prolinols.

Anne Cochi, Domingo Gomez Pardo, Janine Cossy

Index: Org. Lett. 13(16) , 4442-5, (2011)

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Abstract

The activation of N-alkyl prolinols by XtalFluor E allowed the formation of an aziridinium intermediate that can react with tetrabutylammonium azide (nBu(4)NN(3)) to produce 3-azidopiperidines and/or 2-(azidomethyl)pyrrolidines, in a ratio up to 100/0. These 3-azidopiperidines can be reduced to the corresponding 3-aminopiperidines.© 2011 American Chemical Society