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Enantioselective synthesis of α,α-disubstituted-α-amino acids by a sequential nucleophilic addition to nitriles

✍ Scribed by AndréB Charette; Christophe Mellon

Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
683 KB
Volume
54
Category
Article
ISSN
0040-4020

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✦ Synopsis

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.

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Synthesis of α,α-disubstituted-α-amino a
Synthesis of α,α-disubstituted-α-amino acids by double nucleophilic addition to cyanohydrins
✍ AndréB. Charette; Alexandre Gagnon; Marc Janes; Christophe Mellon 📂 Article 📅 1998 🏛 Elsevier Science 🌐 French ⚖ 215 KB

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 a