Tetrahedron Asymmetry p. 699 - 708 (1996)
Update date:2022-08-04
Topics:
Shustov
Rauk
Enantiomers of 3-methylazetidin-2-one - (3R)-(+)- and (3S)-(-)-1 and 3-amino-2-methylpropionic acid - (2R)-(-)- and (2S)-(+)-2 were obtained from corresponding diastereomers of methyl (αS)-N-α-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, (αS)-N-α-methylbenzyl-3-amino-2-methylpropionic acids 5A,B, and (αS)-N-α-methylbenzyl-3-methylazetidin-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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