Amination of α,β-unsaturated (2-trimethylsilanylmethyl) carboxylic esters

✍ Scribed by Tecla Gasperi; M Antonietta Loreto; Paolo A Tardella; Augusto Gambacorta

• Publisher: Elsevier Science
• Year: 2002
• Tongue: French
• Weight: 80 KB
• Volume: 43
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(02)00390-8

✦ Synopsis

The reactions of (2-trimethylsilanylmethyl) a,b-unsaturated carboxylic ethyl esters with NsONHCO 2 Et and CaO produce, after treatment with AcOH, a-methylene N-(ethoxycarbonyl) b-amino carboxylic esters through ring opening and elimination of the trimethylsilyl group from the intermediate aziridine. By ozonization and subsequent reductive cleavage these products give the corresponding N-(ethoxycarbonyl) b-amino a-hydroxy esters.