Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 14, Issue 35, Pages 10958-10966Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200802030
Keywords
amino acids; organo-catalysis; oxazolones; thiourea
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Funding
- Danish National Research Foundation
- OChemSchool
- Ministerio de Edticacion y Ciencia of Spain
- Eusko Jaurlaritza-Gobierno Vasco
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An easy and simple synthetic approach to optically active a,a-quaternary a-amino acids using asymmetric organocatalysis is presented. The addition of oxazolones to nitroalkenes catalyzed by thiourea cinchona derivatives provides the corresponding a,a-quaternary a-amino acid derivatives with good yields, excellent diastereoselectivities (up to 98% dr), and from moderate to good enantioselectivities (up to 92% ee). The reaction can be performed on a large scale. The optically active oxazolone-nitroalkene addition products can be opened in a one-pot reaction to the corresponding ester-amide derivatives. Additional transformations are also presented, such as the synthesis of amino esters, amino acids, and transformation into 3,4-disubstituted pyrrolidin-2-ones.
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