Synthesis of α,α-Disubstituted α-Amino Esters: Nucleophilic Addition to Iminium Salts Generated from Amino Ketene Silyl Acetals
✍ Scribed by Hata, Shingo; Koyama, Hiroshi; Shimizu, Makoto
- Book ID
- 120809078
- Publisher
- American Chemical Society
- Year
- 2011
- Tongue
- English
- Weight
- 294 KB
- Volume
- 76
- Category
- Article
- ISSN
- 0022-3263
No coin nor oath required. For personal study only.
📜 SIMILAR VOLUMES
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
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.