Enantioselective organocatalytic addition of oxazolones to 1,1-bis(phenylsulfonyl)ethylene: A convenient asymmetric synthesis of quaternary α-amino acids

Andrea Nekane R. Alba, Xavier Companyó, Guillem Valero, Albert Moyano, Ramon Rios

Research output: Contribution to journalArticlepeer-review

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Abstract

A new, easy, and highly enantioselective method for the synthesis of quaternary α-alkyl-α-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 α-disubstituted α-amino acid derivatives with complete C4 regioselectivity and with excellent yields and enantioselectivities. This methodology is complementary to previously reported enantioselec-tive approaches to quaternary ot-amino acids and allows the synthesis of αphenyl-α- alkyl-α-amino acids and αiert-butyl-α-alky1-α-amino acids. It has distinct advantages in terms of operational simplicity, enviromentally friendly conditions, and suitability for largescale reactions.

Original languageBritish English
Pages (from-to)5354-5361
Number of pages8
JournalChemistry - A European Journal
Volume16
Issue number18
DOIs
StatePublished - 10 May 2010

Keywords

  • Amino acids michael addition
  • Organocatalysis
  • Oxazolones
  • Stereoselectivity

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