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

Authors
Lee, S Lim, CW Lee, JK Jung, OS Lee, YA
Citation
S. Lee et al., One-pot synthesis of C-2-symmetric N,N '-diaryl bis(oxazolidin-2-ones) as precursors for N,N '-diaryl 2,3-diamino-1,4-butanediols, TETRAHEDR-A, 11(23), 2000, pp. 4709-4717
Citations number
56
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
11
Issue
23
Year of publication
2000
Pages
4709 - 4717
Database
ISI
SICI code
0957-4166(200012)11:23<4709:OSOCN'>2.0.ZU;2-Q
Abstract
A new and general one-pot synthetic method for C-2-symmetric N,N'-aryl-disu bstituted bis(oxazolidin-2-ones) has been developed. Highly regioselective intramolecular cyclization reactions of 2,3-di(methanesulfonyloxy)-1,4-dihy droxybutane with arylisocyanates in the presence of sodium hydride afforded the corresponding C-2-symmetric N,N'-aryl-disubstituted bis(oxazolidin-2-o nes) in 82-92% yields. Hydrolytic ring opening of the bis(oxazolidin-2-ones ) provided a convenient synthetic route for optically pure C-2-symmetric N, N'-aryl-disubstituted 2,3-diamino-1,4-butanediols (58-86% yields). (C) 2001 Elsevier Science Ltd. All rights reserved.