Diastereoselective Alkylation of Chiral Glycinate Derivatives Containing the a-Phenylethyl Group
DOI:
https://doi.org/10.29356/jmcs.v55i3.813Keywords:
Alkylation, diastereoselective, enantioselective, lithium enolates, glycinate, amino acidsAbstract
Novel chiral glycinate derivatives (S)-6 and (S)-7 containing the a-phenylethyl group, were prepared and studied as potential precursors of enantiopure a-substituted-a-amino acids. In particular, the alkylation of enolate (S)-7-Li showed substantial (78:22 dr) stereoinduction by the N-(1-phenylethyl)benzamide chiral auxiliary.
Addition of DMPU showed no appreciable effect upon the diastereoselectivity.
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