New N-terminal prolyl-dipeptide derivatives as organocatalysts for direct asymmetric aldol reaction

Five new N-terminal prolyl-dipeptide derivatives were first synthesized as organocatalyst for the direct asymmetric aldol reaction of acetone and electron-deficient aromatic aldehydes at room temperature. A series of new N-terminal prolyl-dipeptide derivatives have been synthesized and evaluated as...

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Published inTetrahedron letters Vol. 47; no. 44; pp. 7793 - 7796
Main Authors Zheng, Ji-Fu, Li, Yao-Xian, Zhang, Suo-Qin, Yang, Song-Tao, Wang, Xiao-Ming, Wang, Yong-Zhi, Bai, Jie, Liu, Fu-An
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 30.10.2006
Elsevier
Subjects
Asymmetric catalysis
Chemistry
Chemistry, Organic
Direct aldol reaction
N-terminal prolyl-dipeptide derivatives
Organocatalyst
Physical Sciences
Science & Technology
Direct aldol reaction
N-terminal prolyl-dipeptide derivatives
Organocatalyst
Asymmetric catalysis
ACID
MICHAEL
ENANTIOSELECTIVE ALDOL
STRATEGY
ALDEHYDES
asymmetric catalysis
DISCOVERY
PEPTIDES
VERSATILE CATALYSTS
organocatalyst
direct aldol reaction
PROLINE
EFFICIENT
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Summary:Five new N-terminal prolyl-dipeptide derivatives were first synthesized as organocatalyst for the direct asymmetric aldol reaction of acetone and electron-deficient aromatic aldehydes at room temperature. A series of new N-terminal prolyl-dipeptide derivatives have been synthesized and evaluated as organocatalysts for the direct asymmetric aldol reaction of acetone with electron-deficient aromatic aldehydes. At room temperature, the presence of 10 mol % of catalysts 2 and 5 efficiently catalyzes the direct asymmetric aldol reaction to give the aldol adducts with modest to excellent enantiomeric excesses (ee) values, which are up to 96%.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2006.08.084