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Letter

Samarium Diiodide-Catalyzed Diastereoselective Pinacol Couplings

Supporting Info

Helen C. Aspinall, Nicholas Greeves,* and Carine Valla

Donnan and Robert Robinson Laboratories, Department of Chemistry, University of Liverpool, Crown Street, Liverpool, L69 7ZD, UK

Org. Lett., 2005, 7 (10), pp 1919–1922

DOI: 10.1021/ol050256f

Publication Date (Web): April 9, 2005

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, ngreeves@liv.ac.uk

Abstract

A complex of samarium diiodide (SmI₂) with tetraglyme catalyzes the intermolecular pinacol coupling of aromatic or aliphatic aldehydes at loadings of 10 mol % in the presence of Me₂SiCl₂ and Mg. Diastereoselectivity of up to 95/5 (±/meso) has been achieved for aliphatic aldehydes and up to 19/81 (±/meso) for aromatic aldehydes. De values of up to 99% have been achieved in intramolecular pinacol coupling reactions using the SmI₂/tetraglyme/Mg/Me₂SiCl₂ catalytic system.

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Published In Issue May 12, 2005
Received February 7, 2005

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Letter

Samarium Diiodide-Catalyzed Diastereoselective Pinacol Couplings

Abstract

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SciFinder Links

History

Recommend & Share

Related Content

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Tetrabutylammonium Tribromide (TBATB) as An Efficient Generator of HBr for an Efficient Chemoselective Reagent for Acetalization of Carbonyl Compounds

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