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ChemInform Abstract: Synthesis of 3-Hydroxy and 3-Amino 2-Substituted N-Heterocycles via Enamine Oxidation and Aziridination.

✍ Scribed by M. SUNOSE; K. M. ANDERSON; A. G. ORPEN; T. GALLAGHER; S. J. F. MACDONALD

Publisher
John Wiley and Sons
Year
2010
Weight
29 KB
Volume
30
Category
Article
ISSN
0931-7597

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✦ Synopsis

Synthesis of 3-Hydroxy and 3-Amino 2-Substituted N-Heterocycles via Enamine Oxidation and Aziridination.

-Usual asymmetric epoxidation of the N-sulfonyl heterocyclic enamines (I) followed by methanolysis results in formation of 2,3-dihydroxy derivatives. Only diol derivatives are also obtained under Sharpless aminohydroxylation conditions in the presence of chloramine-T. The desired 3-amino derivatives (IV) and (V) are obtained via Mn-mediated aziridination of (Ia). -(SUNOSE, M.; ANDERSON, K. M.;

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