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Aminodiols via stereocontrolled oxidation of methyleneaziridines.

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.

SUBMITTER: Rigoli JW

PROVIDER: S-EPMC3993784 | biostudies-other | 2014 Mar

REPOSITORIES: biostudies-other

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Aminodiols via stereocontrolled oxidation of methyleneaziridines.

Rigoli Jared W JW Guzei Ilia A IA Schomaker Jennifer M JM

Organic letters 20140311 6

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. ...[more]

PMID: 24617556

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