Novel rearrangements of chiral 3-oxazolidinylazetidin-2-ones

✍ Scribed by Iwao Ojima; Yazhong Pei

• Publisher: Elsevier Science
• Year: 1992
• Tongue: French
• Weight: 235 KB
• Volume: 33
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)91567-3

✦ Synopsis

Reaction of a 3-oxazolininyM-hydroxymethylazetidin-2-one with excess NaOh4e in rejluzing methanol gives the corresponding I-oxa-,8-diazabicyclo[4.3.0]nonan-5,9-dione stereospecifcally in nearly quantitative yield via a novel skeletal rearrangement, which includes a gamnu-l&one as a key-intermediate; Possible mechanisms and similar rearrangement in a related system is discussed.

We have been applying our "p-Lactam Synthon Method" to the asymmetric synthesis of various nonprotein amino acids and dipeptldes containing non-protein amino acid residues, * which are potential enzyme