| Enantioselective organocatalytic addition of oxazolones to 1,1-bis(phenylsulfonyl)ethylene: a convenient asymmetric synthesis of quaternary alpha-amino acids. | |
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MedLine Citation:
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PMID: 20209524 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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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 large-scale reactions. |
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Authors:
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Andrea-Nekane R Alba; Xavier Companyó; Guillem Valero; Albert Moyano; Ramon Rios |
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Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't |
Journal Detail:
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Title: Chemistry (Weinheim an der Bergstrasse, Germany) Volume: 16 ISSN: 1521-3765 ISO Abbreviation: Chemistry Publication Date: 2010 May |
Date Detail:
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Created Date: 2010-06-14 Completed Date: 2010-08-18 Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 9513783 Medline TA: Chemistry Country: Germany |
Other Details:
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Languages: eng Pagination: 5354-61 Citation Subset: IM |
Affiliation:
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Department of Organic Chemistry, Universitat de Barcelona, Faculty of Chemistry, Martí i Franquès 1-11, 08028 Barcelona, Spain. |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Amino Acids
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chemical synthesis*,
chemistry Catalysis Ethylenes / chemistry* Magnetic Resonance Spectroscopy Models, Molecular Molecular Structure Oxazolone / chemistry* Solvents / chemistry* Stereoisomerism Structure-Activity Relationship Sulfhydryl Compounds / chemistry* |
| Chemical | |
Reg. No./Substance:
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0/1,1-bis(phenylsulfonyl)ethylene; 0/Amino Acids; 0/Ethylenes; 0/Solvents; 0/Sulfhydryl Compounds; 15646-46-5/Oxazolone |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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