Stereoselective catalytic tishchenko reduction of β-hydroxyketones using scandium triflate

A number of aliphatic and aromatic β-hydroxyketones were reduced to 1,3-diol monoesters by aldehydes in the presence of a catalytic amount of scandium triflate. Chiral substrates were reduced with high 1,3- anti diastereoselectivity. Sc(OTf) 3 catalyses the highly diastereoselective reaction of β-hy...

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Bibliographic Details
Published inTetrahedron letters Vol. 40; no. 52; pp. 9371 - 9374
Main Authors Gillespie, Kevin M., Munslow, Ian J., Scott, Peter
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 24.12.1999
Elsevier
Subjects
aldols
Chemistry
Chemistry, Organic
diastereoselection
Physical Sciences
reduction
scandium
scandium compounds
Science & Technology
scandium
aldols
reduction
scandium compounds
diastereoselection
KETONES
1,3-DIOLS
HYDRIDE
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Summary:A number of aliphatic and aromatic β-hydroxyketones were reduced to 1,3-diol monoesters by aldehydes in the presence of a catalytic amount of scandium triflate. Chiral substrates were reduced with high 1,3- anti diastereoselectivity. Sc(OTf) 3 catalyses the highly diastereoselective reaction of β-hydroxyketones with aldehydes to give anti-1,3-diol monoesters.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(99)01986-3