A new Yb3+-catalyzed pinacol and imine-coupling reaction

Ytterbium triflate, Yb(OTf)(3), catalyzes the intermolecular reductive homocouplings of imines, aldehydes, and ketones at loadings of 5 mol % in the Presence of Mg and Me3SiCl to give isolated yields of up to 95%. Diastereoselectivity of up to 4/96 (dl/meso) is achieved for aromatic aldehydes, up to...

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Bibliographic Details
Published inTetrahedron letters Vol. 51; no. 12; pp. 1558 - 1561
Main Authors Aspinall, Helen C., Greeves, Nicholas, Hin, Shane Lo Fan
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 01.03.2010
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
DIIODIDE
DIASTEREOSELECTIVE SYNTHESIS
COMPLEXES
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Summary:Ytterbium triflate, Yb(OTf)(3), catalyzes the intermolecular reductive homocouplings of imines, aldehydes, and ketones at loadings of 5 mol % in the Presence of Mg and Me3SiCl to give isolated yields of up to 95%. Diastereoselectivity of up to 4/96 (dl/meso) is achieved for aromatic aldehydes, up to 100% dl for aliphatic aldehydes, and 100% dl for an intramolecular imine coupling. (C) 2010 Elsevier Ltd. All rights reserved.
ISSN:0040-4039
DOI:10.1016/j.tetlet.2010.01.057