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ChemInform Abstract: Facile Synthesis of (S)-β-Hydroxy-β-trichloromethylated Aromatic Ketones by the Regioselective Ring Cleavage of Chiral β- Trichloromethyl-β-propiolactone under the Friedel-Crafts Conditions.

✍ Scribed by T. FUJISAWA; T. ITO; K. FUJIMOTO; M. SHIMIZU; H. WYNBERG; E. G. J. STARING

Publisher: John Wiley and Sons
Year: 2010
Weight: 33 KB
Volume: 28
Category: Article
ISSN: 0931-7597
DOI: 10.1002/chin.199725076

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✦ Synopsis

Facile Synthesis of (S)-β-Hydroxy-β-trichloromethylated Aromatic Ketones by the Regioselective Ring Cleavage of Chiral β-Trichloromethyl-β-propiolactone under the Friedel-Crafts Conditions. -The enantiopure lactone (I) undergoes regioselective Friedel-Crafts acylation with a variety of arenes to give acylated products bearing a chiral trichloromethyl carbonyl moiety. Product (IIIa) is useful as precursor of the ACE inhibitor enalapril.

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