A solid phase synthetic method for amino acids is developed. The N-acetyl-dehydroalanine is quantitatively bound to Wang resin by the Mitsunobu method. Then a Michael addition is achieved on the double bond with different nucleophiles. Non proteinic N-acetyl-ct-amino acids are obtained after cleavag
Solid-phase synthesis of α-amino acids by radical addition to adehydroalanine derivative
✍ Scribed by Anne-Marie Yim; Yves Vidal; Philippe Viallefont; Jean Martinez
- Publisher
- Elsevier Science
- Year
- 1999
- Tongue
- French
- Weight
- 210 KB
- Volume
- 40
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
The first synthesis of N-aceOd-wamina acids by radical addition on solid support to commercialy available 2-acetamidoacrylic acid ~tng the merctey method is described The reaction proceeds in acceptable chemical efficiency (49-60~) depending on the nature of the mercury halide agent. Cleavage by mild acid treatment released the prodact from the solid support in excellent purity.
📜 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.