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
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
10 May 2010
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), .
(doi:10.1002/chem.200903025).
(PMID:20209524)
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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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: http://eprints.soton.ac.uk/id/eprint/340219
ISSN: 0947-6539
PURE UUID: 60c29ea2-e97f-4fcb-afa3-933718d19a1b
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Date deposited: 15 Jun 2012 12:17
Last modified: 14 Mar 2024 11:20
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Contributors
Author:
Andrea-Nekane R. Alba
Author:
Xavier Companyó
Author:
Guillem Valero
Author:
Albert Moyano
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