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New synthetic routes to β-fluoro-α-aminoacids B - from glycidonitriles

✍ Scribed by A.I. Ayi; M. Remli; R. Guedj

Publisher
Elsevier Science
Year
1980
Tongue
English
Weight
61 KB
Volume
16
Category
Article
ISSN
0022-1139

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✦ Synopsis

Ring opening of the glycidonitriles (II a-e) by HF/pyridine leads to the fluorocyanohydrins (III a-e). Treatment of the fluorocyanohydrins with ammonia in anhydrous methanol gives the a-amino-6-fluoronitriles (IV a-e) which upon acidic hydrol sis afford the s-fluoro-a-aminoacids (V a-e) in good overall yield.

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A new sequential defluorination route to
A new sequential defluorination route to α-fluoro-α,β-unsaturated ketones from trifluoromethyl ketones
✍ Hiroshi Hata; Takeshi Kobayashi; Hideki Amii; Kenji Uneyama; John T. Welch 📂 Article 📅 2002 🏛 Elsevier Science 🌐 French ⚖ 284 KB

a-Fluoro-a,b-unsaturated ketones were prepared from trifluoromethyl ketones via a sequence involving Mg metal promoted successive double defluorination. Trifluoromethyl ketones were transformed to b,b-difluoroenol silyl ethers which were then coupled with aldehydes and ketones to b-hydroxy-a,a-diflu