Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 16, Issue 18, Pages 5354-5361Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200903025
Keywords
amino acids; Michael addition; organocatalysis; oxazolones; stereoselectivity
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Funding
- Spanish Ministry of Science and Innovation (MICINN) [AYA2009-13920-C02-02]
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A new, easy, and highly enantioselective method for the synthesis of quaternary alpha-alkyl-alpha-amino acids based on organocatalysis is reported. The addition of oxazolones to 1,1-bis(phenylsulfonyl)ethylene is efficiently catalyzed by simple chiral bases or thioureas. The reaction affords alpha,alpha-disubstituted alpha-amino acid derivatives with complete C4 regioselectivity and with excellent yields and enantioselectivities. This methodology is complementary to previously reported enantioselective approaches to quaternary alpha-amino acids and allows the synthesis of alpha-phenyl-alpha-alkyl-alpha-amino acids and alpha-tert-butyl-alpha-alkyl-alpha-amino acids. It has distinct advantages in terms of operational simplicity, enviromentally friendly conditions, and suitability for largescale reactions.
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