✦ LIBER ✦
From pyrrolidin-2-ones to 3-aza-2-oxobicyclo[3.2.0]heptanes. Synthesis of both enantiomers of cis-2-aminomethylcyclobutane carboxylic acid, a conformationally restricted analogue of GABA
✍ Scribed by Roberta Galeazzi; Giovanna Mobbili; Mario Orena
- Publisher
- Elsevier Science
- Year
- 1999
- Tongue
- French
- Weight
- 563 KB
- Volume
- 55
- Category
- Article
- ISSN
- 0040-4020
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✦ Synopsis
By changing the cyclisation conditions (Nail in THF or NaOEt in EtOH), an enantiopure malonamide containing an enoate acceptor afforded either diastereomeric pyrrolidin-2-one 3 or 4 as the major product of the intramolecular conjugate addition. After separation, both diastereomers were converted through simple steps into the corresponding 3-aza-2oxobicyclo[32.0] heptane which eventually led to each enantiomer of cis-2aminomethylcyclobutanecarboxylic acid, 1, a conformationally restricted analogue of GABA, in both enantiomerically pure form.