Synthesis of protected, chiral α,α-disubstituted α-amino acids via a Beckmann rearrangement
✍ Scribed by Rogelio P. Frutos; Denice M. Spero
- Publisher
- Elsevier Science
- Year
- 1998
- Tongue
- French
- Weight
- 202 KB
- Volume
- 39
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
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.
📜 SIMILAR VOLUMES
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.
An efficient route for the asymmetric synthesis of ct,a-disubstituted or-amino acids derivatives (1, 2, and 3) starting from readily available epoxy silyl ethers (6) has been developed. High enantiomeric purity can be realized by the present method using a combination of MABR rearrangement of a chir