Asymmetric Synthesis of an Unusual Amino Acid: Synthesis of Four Isomers of β-Methyl-3-(2'-naphthyl)alanine. -Using (R)-4phenyloxazolidinone (II) as chiral auxiliary, the synthesis of the optically pure amino acid (VIII) is achieved by diastereoselective methylation followed by indirect azidation a
Asymmetric synthesis of unusual amino acid: Synthesis of four isomers of β-methyl-3-(2′-naphthyl)alanine
✍ Scribed by Wei Yuan; Victor J. Hruby
- Publisher
- Elsevier Science
- Year
- 1997
- Tongue
- French
- Weight
- 173 KB
- Volume
- 38
- Category
- Article
- ISSN
- 0040-4039
No coin nor oath required. For personal study only.
✦ Synopsis
The synthesis of all four individual isomers of 3-methyl-3-(2'-naphthyl)analine was accomplished using asymmetric conjugate 1 A-addition followed by direct or indirect azidation using an Evans-type chiral auxiliary (4-phenyl-2-oxazolidinone).
📜 SIMILAR VOLUMES
All the four individual isomers of R-methylphenylalanine have been synthesized in very high optical purities by utilizing in part the chiral imide enolate bromination methodology of Evans and co-workers. Substitution of the diastereotopic X-hydrogens of many a-amino acids provides inprinciple, an a
We have developed methods for the synthesis of the four optically pure isomers of B-methyltryptophan with the 2-mesitylenesulfonyl indole protecting group for peptide synthesis. Starting from 3-indoleacrylic acid, the Bmethyl function was generated by a chiral auxiliary-directed asymmetric conjugate