Application of the Ester Enolate Claisen Rearrangement in the Synthesis of Amino Acids Containing Quaternary Carbon Centers
β Scribed by Kazmaier, Uli
- Book ID
- 127354051
- Publisher
- American Chemical Society
- Year
- 1996
- Tongue
- English
- Weight
- 173 KB
- Volume
- 61
- Category
- Article
- ISSN
- 0022-3263
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π SIMILAR VOLUMES
## Abstract Deprotonation of __N__βprotected amino acid allylic esters with LDA at β78Β°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 __Ξ³,Ξ΄__βunsaturat
The Claisen rearrangement of N-BOC-glycinate esters 1a-1d led to the formation of a-allylsilane-functionalized amino acids 2-3 in good yield (up to 80%). The diastereoselectivity of the reaction varied from 2:1 to 29:1 (syn:anti ) for 1a depending on reaction conditions. In the case of the Ireland-C