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

Enantioselective organocatalytic addition of oxazolones to 1,1-bis(phenylsulfonyl)ethylene: a convenient asymmetric synthesis of quaternary alpha-amino acids
Enantioselective organocatalytic addition of oxazolones to 1,1-bis(phenylsulfonyl)ethylene: a convenient asymmetric synthesis of quaternary alpha-amino acids
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.
amino acids, michael addition, organocatalysis, oxazolones, stereoselectivity
0947-6539
5354-5361
Alba, Andrea-Nekane R.
d1750aca-a087-449c-8466-11fb54264bea
Companyó, Xavier
446791db-6e0a-40f9-9f20-3a8e8af9803c
Valero, Guillem
c5f692fe-3b07-4916-a4ec-23f78a45cc15
Moyano, Albert
07f92405-40f4-4fc4-97b3-9bd5c9c14baa
Rios, Ramon
609bedf2-e886-4d62-a676-a32b6f8c1441
Alba, Andrea-Nekane R.
d1750aca-a087-449c-8466-11fb54264bea
Companyó, Xavier
446791db-6e0a-40f9-9f20-3a8e8af9803c
Valero, Guillem
c5f692fe-3b07-4916-a4ec-23f78a45cc15
Moyano, Albert
07f92405-40f4-4fc4-97b3-9bd5c9c14baa
Rios, Ramon
609bedf2-e886-4d62-a676-a32b6f8c1441

Alba, Andrea-Nekane R., Companyó, Xavier, Valero, Guillem, Moyano, Albert and Rios, Ramon (2010) Enantioselective organocatalytic addition of oxazolones to 1,1-bis(phenylsulfonyl)ethylene: a convenient asymmetric synthesis of quaternary alpha-amino acids. Chemistry - A European Journal, 16 (18), 5354-5361. (doi:10.1002/chem.200903025). (PMID:20209524)

Record type: Article

Abstract

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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More information

e-pub ahead of print date: 5 March 2010
Published date: 10 May 2010
Keywords: amino acids, michael addition, organocatalysis, oxazolones, stereoselectivity
Organisations: Chemistry

Identifiers

Local EPrints ID: 340219
URI: https://eprints.soton.ac.uk/id/eprint/340219
ISSN: 0947-6539
PURE UUID: 60c29ea2-e97f-4fcb-afa3-933718d19a1b
ORCID for Ramon Rios: ORCID iD orcid.org/0000-0002-3843-8521

Catalogue record

Date deposited: 15 Jun 2012 12:17
Last modified: 20 Jul 2019 00:42

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Contributors

Author: Andrea-Nekane R. Alba
Author: Xavier Companyó
Author: Guillem Valero
Author: Albert Moyano
Author: Ramon Rios ORCID iD

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