Easy access to orthogonally protected α-alkyl aspartic acid and α-alkyl asparagine derivatives by controlled opening of β-lactams

✍ Scribed by Guillermo Gerona-Navarro; Ma̱ Teresa Garcı́a-López; Rosario González-Muñiz

• Book ID: 104254077
• Publisher: Elsevier Science
• Year: 2003
• Tongue: French
• Weight: 120 KB
• Volume: 44
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(03)01453-9

✦ Synopsis

The controlled opening of the N1 C2 bond in 1-carbamate-substituted 2-azetidinones derived from amino acids by Oand N-nucleophiles provided a straightforward access to orthogonally protected a-alkyl aspartic acid and asparagine derivatives. The use of DBU or sodium azide as additive is essential for expedient cleavage by amino acids to the corresponding b-aspartic acid dipeptides.