Samarium Diiodide-Catalyzed Diastereoselective Pinacol Couplings

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, Email: ngreevesliv.ac.uk

H. C. Aspinall, N. Greeves, C. Valla, Org. Lett., 2005, 7, 1919-1922.

DOI: 10.1021/ol050256f

---

Abstract

An intermolecular pinacol coupling of aromatic or aliphatic carbonyl compounds catalyzed by a complex of samarium diiodide (SmI₂) with tetraglyme in the presence of Me₂SiCl₂ and Mg is described. High diastereoselectivity has been achieved in reactions with aliphatic and aromatic aldehydes. De values of up to 99% have been achieved in intramolecular pinacol coupling reactions.

see article for more examples

---

---

Key Words

Pinacol Coupling Reaction, Samarium Diiodide, Magnesium

---

ID: J54-Y2005-550