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Synthesis of α,α-disubstituted-α-amino acids by double nucleophilic addition to cyanohydrins

✍ Scribed by AndréB. Charette; Alexandre Gagnon; Marc Janes; Christophe Mellon

Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
215 KB
Volume
39
Category
Article
ISSN
0040-4039

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✦ Synopsis

The synthesis of tertiary carbinamines was achieved by the double nucleophilic addition of Grignard reagents to cyanohydrins. Titanium isopropoxide was found to promote the process.

In a typical example, the rapid conversion of a carbinamine to the coresponding o~.o~-disubstitutedct-aminoacid was also demonstrated.

📜 SIMILAR VOLUMES

Enantioselective synthesis of α,α-disubs
Enantioselective synthesis of α,α-disubstituted-α-amino acids by a sequential nucleophilic addition to nitriles
✍ AndréB Charette; Christophe Mellon 📂 Article 📅 1998 🏛 Elsevier Science 🌐 French ⚖ 683 KB

The sequential addition of two different nucleophiles to a tartaric acid-derived nitrile produced carbinamines. The adducts from chelation-controlled addition which are obtained in high diastereoselectivities and yields, were easily converted to ct,ct-disubstituted-t~-amino acids.