Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2009, Issue 27, Pages 4622-4626Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.200900547
Keywords
Amino acids; Asymmetric catalysis; Carbohydrates; Organocatalysis
Categories
Funding
- National Natural Science Foundation of China [20702044]
- Yunnan Province Government [2008CD064]
- Yunnan University
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Bifunctional chiral tertiary amine thioureas derived from both alpha-amino acids and carbohydrates were developed. These organocatalysts promoted the enantioselective conjugate addition of acetylacetone to various aromatic and aliphatic nitroolefins at room temperature in good yields (up to 93%) and with good enantioselectivity (up to 90% ee). Furthermore, an interesting matched-mismatched effect of two different chiral units in a chiral organocatalyst was disclosed. Both enantiomers of a product can be achieved in almost the same enantiomeric excess with the matched and mismatched chiral organocatalysts simply by changing the solvent from THF to toluene. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
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