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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 Tamotsu Fujisawa; Takatoshi Ito; Kenji Fujimoto; Makoto Shimizu; H. Wynberg; E.G.J. Staring

Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
259 KB
Volume
38
Category
Article
ISSN
0040-4039

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✦ Synopsis

The reaction of enantiomerically pure [3-~ichloromethyl-13-propiolactone (1) as a chiral building block with an aromatic compound in the presence of Lewis acid provided an acylated product with a chiral trichloromethyl carbinol moiety. The acylated product was used as an effective chiral synthon for natural product synthesis such as enalapril of ACE inhibitor.

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ChemInform Abstract: Facile Synthesis of
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.
✍ T. FUJISAWA; T. ITO; K. FUJIMOTO; M. SHIMIZU; H. WYNBERG; E. G. J. STARING 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 33 KB 👁 1 views

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 giv