Samarium diiodide-catalyzed diastereoselective pinacol couplings |
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Authors: | Aspinall Helen C Greeves Nicholas Valla Carine |
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Institution: | Donnan and Robert Robinson Laboratories, Department of Chemistry, University of Liverpool, UK. |
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Abstract: | A complex of samarium diiodide (SmI(2)) with tetraglyme catalyzes the intermolecular pinacol coupling of aromatic or aliphatic aldehydes at loadings of 10 mol % in the presence of Me(2)SiCl(2) 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 SmI(2)/tetraglyme/Mg/Me(2)SiCl(2) catalytic system. |
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