CHIRAL OXAZOLIDINONES FROM N-BOC DERIVATIVES OF BETA-AMINO ALCOHOLS -EFFECT OF A N-METHYL SUBSTITUENT ON REACTIVITY AND STEREOSELECTIVITY

Authors
AGAMI C COUTY F HAMON L VENIER O
Citation
C. Agami et al., CHIRAL OXAZOLIDINONES FROM N-BOC DERIVATIVES OF BETA-AMINO ALCOHOLS -EFFECT OF A N-METHYL SUBSTITUENT ON REACTIVITY AND STEREOSELECTIVITY, Tetrahedron letters, 34(28), 1993, pp. 4509-4512
Citations number
26
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
34
Issue
28
Year of publication
1993
Pages
4509 - 4512
Database
ISI
SICI code
0040-4039(1993)34:28<4509:COFNDO>2.0.ZU;2-Z
Abstract
Treatment of N-tert-butoxycarbonyl derivatives of homochiral beta-amin o alcohols with p-toluenesulfonyl chloride affords 2-oxazolidinones. T hese heterocycles were produced by intramolecular nucleophilic attack of the carbamate moiety in an intermediate tosylate. The presence of a N-methyl substituent enhanced the cyclization rate and this effect wa s studied by AMI calculations.