Syntheses of protected vinylic amino acids by intermolecular Lewis acid catalyzed ene reactions

✍ Scribed by K. Agouridas; J.M. Girodeau; R. Pineau

• Book ID: 104228784
• Publisher: Elsevier Science
• Year: 1985
• Tongue: French
• Weight: 212 KB
• Volume: 26
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)98632-5

✦ Synopsis

Intermolecular ene reaction between ethylglyoxylate and allylic amino acid derivatives gave highly functionalized unsaturated pimelic acids in one step. This synthetic approach appears as a new efficient method for the synthesis of vinylic amino acids. Vinylic amino acids are biochemically and pharmacologically important molecules 1 . Chemically no direct access to vinylic amino acids is available. For the synthesis of vinylic 2,6_diaminopimelic acid derivatives, part of our antibiotic program, we needed an efficient and rapid method for the synthesis of the seven carbon backbone of pimelic acid containing a double bond. Snider 2 and Achmatouicz 3 described the synthesis of allylic amino acids by the ene-reaction. It appeared to us that if derivatives of allylglycine could react with