Synthesis of sterically high demanding α-alkylated amino acids via Claisen rearrangement of chelated enolates
✍ Scribed by Uli Kazmaier; Sabine Maier
- Publisher
- Elsevier Science
- Year
- 1996
- Tongue
- French
- Weight
- 651 KB
- Volume
- 52
- Category
- Article
- ISSN
- 0040-4020
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Asymmetric Ester Enolate Claisen Rearrangement as a Suitable Method for the Synthesis of Sterically Highly Demanding Amino Acids. -The highly diastereo-and enantioselective synthesis of otherwise difficult to obtain γ,δ-unsaturated amino acids containing β-quaternary carbon centers (cf. (III), (V);
## Abstract Deprotonation of __N__‐protected amino acid allylic esters with LDA at −78°C and subsequent addition of a metal salt presumably results in the formation of a chelated metal enolate that undergoes Claisen rearrangement upon warming up to room temperature, giving rise to __γ,δ__‐unsaturat