Synthesis of a series of polar, orthogonally protected, α,α-disubstituted amino acids
✍ Scribed by T.Scott Yokum; Matthew G. Bursavich; Sarina A. Piha-Paul; David A. Hall; Mark L. McLaughlin
- Publisher
- Elsevier Science
- Year
- 1997
- Tongue
- French
- Weight
- 264 KB
- Volume
- 38
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
The synthesis of four novel, "cationic", a,u-disubstituted amino acids is described. The new amino acids use an orthogonal protection scheme making them suitable for incorporation via solid-phase peptide synthesis.
📜 SIMILAR VOLUMES
The synthesis of chiral, nonracemic, fully protected a,a-disubstituted a-amino acids via the Beckmann rearrangement of tosylated oximes 1 is described. The desired amino acids were obtained in good yields with excellent enantioseleetivities in relatively few steps.
## Abstract For Abstract see ChemInform Abstract in Full Text.
Copper(salen) complex 1 has been found to catalyse the asymmetric alkylation of enolates derived from a variety of amino acids. There is a clear relationship between the size of the side chain in the substrate and the enantioselectivity of the process, so that the enantioselectivity decreases in the