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3-Methylazetidin-2-one and its precursors: Optical resolution and absolute configurations

✍ Scribed by G.V. Shustov; A. Rauk

Publisher: Elsevier Science
Year: 1996
Tongue: English
Weight: 531 KB
Volume: 7
Category: Article
ISSN: 0957-4166
DOI: 10.1016/0957-4166(96)00065-1

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✦ Synopsis

Enantiomers of 3-methylazetidin-2-one -(3R)-(+)-and (3S)-(-)-1 and of 3-amino-2methylpropionic acid -(2R)-(-)-and (2S)-(+)-2 were obtained from corresponding diastereomers of methyl (ty.S)-N-t~-methylbenzyl-3-amino-2-methylpropionate 3A,B which had been separated by recrystallization of their salts 4A,B with p-toluenesulfonic acid. The absolute configurations of azetidinones (+)-and (-)-1 and their diastereomeric precursors, i.e. amino esters 3A,B, (tyS)-N-et-methylbenzyl-3-amino-2-methylpropionic acids 5A,B, and (~S)-N-t~-methylbenzyl-3methylazetidin-2-ones 6A,B were established by conversion of (+)-1 to amino acid (2R)-(-)-2 and of amino acid (2S)-(+)-2 to (-)-1.

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