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Electrogenerated Chiral 4-Methoxy-2-oxazolidinones as Diastereoselective Amidoalkylation Reagents for the Synthesis of β-Amino Alcohol Precursors

✍ Scribed by Kerstin Schierle-Arndt; Doris Kolter; Karsten Danielmeier; Eberhard Steckhan

Publisher: John Wiley and Sons
Year: 2001
Tongue: English
Weight: 365 KB
Volume: 2001
Category: Article
ISSN: 1434-193X
DOI: 10.1002/1099-0690(200107)2001:13<2425::aid-ejoc2425>3.0.co;2-2

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✦ Synopsis

A flexible and efficient synthesis of enantiomerically pure 4,5-substituted 2-oxazolidinonesimportant target molecules as precursors of pharmacologically active 2-oxazolidinones, β-amino alcohols, β-blockers and azasugar derivatives is described. As starting materials, the enantiopure storage forms of chiral N-acyliminium ions (4RS,5S)-5-chloromethyl-4-methoxy-1,3-oxazolidin-2-one ( 2) and (4RS,5R)-4-methoxy-5-methyl-1,3-oxazolidin-2-one (3) were used; these are [a] Kekule ´-Institut für Organische Chemie und Biochemie der

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