An efficient synthesis of γ-amino β-ketoester by cross-Claisen condensation with α-amino acid derivatives

✍ Scribed by Yutaka Honda; Satoshi Katayama; Mitsuhiko Kojima; Takayuki Suzuki; Kunisuke Izawa

• Publisher: Elsevier Science
• Year: 2003
• Tongue: French
• Weight: 202 KB
• Volume: 44
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(03)00464-7

✦ Synopsis

Cross-ester condensation between N-protected amino acid ester and the lithium enolate prepared from alkyl acetate gave the corresponding b-ketoester in high yield without the formation of the tertiary alcohol that is commonly seen as by-product. This interesting reaction is applicable to the amino acid derivatives with suitable N-protecting groups, which can help to stabilize the reaction intermediates.