Lewis Acid Catalyzed Intramolecular Allylic Substitution of Bis(trichloroacetimidates): A Versatile Approach to Racemic Unsaturated Amino Acids

✍ Scribed by Liene Grigorjeva; Aigars Jirgensons

• Publisher: John Wiley and Sons
• Year: 2011
• Tongue: English
• Weight: 220 KB
• Volume: 2011
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/ejoc.201100060

✦ Synopsis

Abstract

Lewis acid catalyzed cyclization of trichloroacetimidates derived from 1,4‐butenediols and 1,5‐butenediols was achieved to give 4‐vinyl oxazolines and 4‐vinyloxazines in good to excellent yields. The cyclization products were transformed to protected unsaturated α‐ and β‐amino acids, thus demonstrating the novel approach to access these important classes of compounds.