One-pot synthesis of C2-symmetric N,N′-diaryl bis(oxazolidin-2-ones) as precursors for N,N′-diaryl 2,3-diamino-1,4-butanediols

Sang Gi Lee, Chung Woo Lim, Jae Kyun Lee, Ok Sang Jung, Young A. Lee

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Abstract

A new and general one-pot synthetic method for C2-symmetric N,N′-aryl-disubstituted bis(oxazolidin-2-ones) has been developed. Highly regioselective intramolecular cyclization reactions of 2,3-di(methanesulfonyloxy)-1,4-dihydroxybutane with arylisocyanates in the presence of sodium hydride afforded the corresponding C2-symmetric N,N′-aryl-disubstituted bis(oxazolidin-2-ones) in 82-92% yields. Hydrolytic ring opening of the bis(oxazolidin-2-ones) provided a convenient synthetic route for optically pure C2-symmetric N,N′-aryl-disubstituted 2,3-diamino-1,4-butanediols (58-86% yields).

Original languageEnglish
Pages (from-to)4709-4717
Number of pages9
JournalTetrahedron Asymmetry
Volume11
Issue number23
DOIs
StatePublished - 1 Dec 2000

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