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Synthesis of a potential intermediate to β-lactam antibiotics

✍ Scribed by Andrew Freer; Karl Overton; Richard Tomanek

Publisher
Elsevier Science
Year
1990
Tongue
French
Weight
170 KB
Volume
31
Category
Article
ISSN
0040-4039

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✦ Synopsis

Cycloaddition of nitrone (2) to a-chloroacrylonitrile followed by hydrolysis afforded the isoxazolidinone (I) as a single diastereomer.

📜 SIMILAR VOLUMES

Diastereoselective synthesis of a key in
Diastereoselective synthesis of a key intermediate for the preparation of tricyclic β-lactam antibiotics
✍ Takaji Matsumoto; Toshiyuki Murayama; Shigeru Mitsuhashi; Takashi Miura 📂 Article 📅 1999 🏛 Elsevier Science 🌐 French ⚖ 236 KB

Asymmetric synthesis of (S)-5 has been accomplished with an excellent enantiomeric excess by hydrogenation of raeemie 5 using ruthenium-BINAP-diamine-KOH system, followed by oxidation. Magnesium enolate of (2S)-2-methoxycyclohexanone [(S)-5] reacts with the 4-aeetoxyazetidinone 4 to give the key int