The tetrahydrooxazinone way to enantiopure α-amino acids: Synthesis of cis and trans 3-vinyl pipecolic acids via an intramolecular reaction between an iminium ion and an allylsilane moieties

✍ Scribed by Claude Agami; Dominique Bihan; Louis Hamon; Catherine Puchot-Kadouri

• Publisher: Elsevier Science
• Year: 1998
• Tongue: French
• Weight: 500 KB
• Volume: 54
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(98)00486-4

✦ Synopsis

Reaction of glyoxal with a derivative of (R)-phenylglycinol having an allylsilane side-chain afforded a transient iminium ion. Intramolecular reaction of the iminium ion and the allylsilane moieties occurred in a totally stereoselective way. Straightforward transformations ultimately led to enanfiopure either cis or trans 3vinyl pipecolic acid methyl ester. The stereochemical course of this reaction was rationalized via AMI calculations.