Journal
SYNTHESIS-STUTTGART
Volume 45, Issue 10, Pages 1312-1318Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0032-1318506
Keywords
unnatural amino acid; monoesterification; half-ester; biaryl; axial chirality
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Funding
- Ministry of Education, Culture, Sports, Science and Technology, Japan
- Grants-in-Aid for Scientific Research [23590006] Funding Source: KAKEN
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Axially chiral amino acid derivatives were synthesized via a selective single-step monoesterification of 1,1'-binaphthyl-2,2'-dicarboxylic acids. In the presence of Ag2CO3, the alkylative monoesterification of a 1,1'-binaphthyl-2,2'-dicarboxylic acid with an alkyl halide proceeded selectively in a single operation. Curtius rearrangement of the monomethyl ester and successive alcoholysis of the corresponding isocyanate afforded the N-protected binaphthyl amino acids.
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