Aminodiols via stereocontrolled oxidation of methyleneaziridines

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Abstract

A highly diastereoselective Ru-catalyzed oxidation/reduction sequence of bicyclic methyleneaziridines provides a facile route to complex 1-amino-2,3-diol motifs. The relative anti stereochemistry between the amine and the vicinal alcohol are proposed to result from 1,3-bischelation in the transition state by the C1 and C3 heteroatoms. © 2014 American Chemical Society.

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Rigoli, J. W., Guzei, I. A., & Schomaker, J. M. (2014). Aminodiols via stereocontrolled oxidation of methyleneaziridines. Organic Letters, 16(6), 1696–1699. https://doi.org/10.1021/ol5003576

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