ChemInform Abstract: 2-Amino-1-phenyl-propan-1,3-diol as Chiral Auxiliary. Application in the Synthesis of cis 3-Phthalimido-4-styryl-2-azetidinones.

✍ Scribed by T. E. GUNDA; F. SZTARICSKAI

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 36 KB
• Volume: 28
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199743039

✦ Synopsis

1997 stereochemistry stereochemistry (general, optical resolution) O 0030

43 -039

2-Amino-1-phenyl-propan-1,3-diol as Chiral Auxiliary. Application in the Synthesis of cis 3-Phthalimido-4-styryl-2-azetidinones.

-The title N-protected azetidinones like (IV), (V), and (XI) are obtained in optically pure form by chiral Staudinger reaction. Only cis products are isolated with the β-isomers as major ones. The cis-α/β ratio can be influenced by different protective silyl groups of the diol moiety. The removal of the propanediol moiety is accomplished either by regioselective acetylation, double bond formation and subsequent oxidation as is shown for phenylpropyl protected (IV), or by direct oxidation and removal of the diketo moiety as is tested with nitropropyl compound (XI). -(GUNDA, T.