Two-carbon ring expansion of β-lactams via N(1)C(4) cleavage reactions

✍ Scribed by Larry A. Cabell; John S. McMurray

• Book ID: 104250742
• Publisher: Elsevier Science
• Year: 2002
• Tongue: French
• Weight: 57 KB
• Volume: 43
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(02)00318-0

✦ Synopsis

The base-catalyzed ring opening of 4-(4%-hydroxyphenyl)-azetidine-2-ones with potassium tert-butoxide in the presence of tert-butyl methyl malonate gave 1,3,4,5-substituted glutarimides in a simple and efficient manner. The glutarimides were formed stereoselectively depending on the size of the 3-substituent of the b-lactam.