Synthesis of the first water-soluble C-2-symmetric bis(oxazolidinone) as apotential bifunctional chiral auxiliary

Authors
Lee, SG Lim, CW Kim, DC Lee, JK
Citation
Sg. Lee et al., Synthesis of the first water-soluble C-2-symmetric bis(oxazolidinone) as apotential bifunctional chiral auxiliary, TETRAHEDR-A, 11(7), 2000, pp. 1455-1458
Citations number
26
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
11
Issue
7
Year of publication
2000
Pages
1455 - 1458
Database
ISI
SICI code
0957-4166(20000420)11:7<1455:SOTFWC>2.0.ZU;2-O
Abstract
The first water-soluble C-2-symmetric bis(oxazolidinone) 1, a potential bif unctional chiral auxiliary, has been synthesized via regioselective intramo lecular cyclization of a biscarbamate. The sodium enolate derived from N,N' -di(phenylacetyl)bis(oxazolidinone) 7 reacts with methyl iodide with high f acial selectivity (95:5). (C) 2000 Elsevier Science Ltd. All rights reserve d.