Study on improved diastereoselectivity in photo-induced electron transfer pinacol coupling reactions of substituted acetophenones

A novel diastereoselective photo-induced pinacol coupling reactions of substituted acetophenones by electron transfer photosensitization using triethylamine and chiral tertiary amines as electron donating co-sensitizers were investigated in β-CD. Novel diastereoselective photo-induced pinacol coupli...

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Bibliographic Details
Published in:Tetrahedron letters 2011-02, Vol.52 (6), p.718-720
Main Authors: Ma, Nan, Shi, Wei, Zhang, Ronghua, Zhu, Zhiliang, Jiang, Zhiqin
Format: Article
Language:English
Subjects:
Acetophenone
Acetophenones
Amines
Chemical reactions
Chiral tertiary amines
Cyclodextrins
Diastereoselectivity
Photo-pinacol coupling
Solvents
Tetrahedrons
Triethylamine
Zeolites
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Summary:A novel diastereoselective photo-induced pinacol coupling reactions of substituted acetophenones by electron transfer photosensitization using triethylamine and chiral tertiary amines as electron donating co-sensitizers were investigated in β-CD. Novel diastereoselective photo-induced pinacol coupling reactions of acetophenones by using triethylamine and chiral tertiary amines as electron donating co-sensitizers were studied. Various influence factors including solvents, substituents, and chiral amines on both the diastereoselectivity and yield were examined. The diastereoselectivities were enhanced in supramolecular systems of cyclodextrins and zeolites. The best result of dl/ meso up to 82:18 was obtained in combination use of chiral tertiary amine and β-CD.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2010.12.007