Stereospecific rearrangements of optically active 2-aryl-3-ethenyloxiranes to give optically active β-ethenylbenzeneethanols: Benzyl vs. allyl cations and an efficient synthesis of (S)-ibuprofen

✍ Scribed by Michael E. Jung; Karen L. Anderson

• Publisher: Elsevier Science
• Year: 1997
• Tongue: French
• Weight: 198 KB
• Volume: 38
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(97)00425-5

✦ Synopsis

Rearrangements of aryl-and ethenyl-substituted oxiranes proceed well in the presence of triethylsilane and BF 3 to give optically active alcohols, which we have used for a synthesis of (S)-ibuprofen 1. We have also shown that a vinyl group migrates to a benzylic cation faster than a phenyl group migrates to an allyl cation.