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Application of the Ester Enolate Claisen Rearrangement in the Synthesis of Amino Acids Containing Quaternary Carbon Centers

✍ 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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## Abstract Deprotonation of __N__‐protected amino acid allylic esters with LDA at βˆ’78Β°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΄__‐unsaturat

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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