4.5 Article

Phase- Transfer- Catalyzed Asymmetric a- Arylation of a- Amino Acid Derivatives

Journal

ASIAN JOURNAL OF ORGANIC CHEMISTRY
Volume 3, Issue 4, Pages 433-436

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ajoc.201400004

Keywords

amino acids; aryl triflates; organocatalysis; phase-transfer catalysis; synthetic methods

Funding

  1. JSPS
  2. MEXT (Japan)
  3. Grants-in-Aid for Scientific Research [24106716, 21000006, 26220803] Funding Source: KAKEN

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Highly enantioselective -arylation of -amino acid derivatives via nucleophilic aromatic substitution (SNAr) was achieved under phase-transfer conditions. Various kinds of -amino acids and aryl triflates containing a nitro group can be tolerated in this reaction to give ,-disubstituted -amino acids in good to high enantioselectivity. This reaction demonstrates a valuable method for the catalytic asymmetric synthesis of ,-disubstituted -amino acids containing an aromatic substituent.

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