C-C Coupling of Ethanol and Dienes

Significance

The Krische group reports a dia­stereoselective ruthenium-catalyzed C-C coupling of ethanol and dienes. The group has extensively studied transfer hydrogenation and this work further expands their efforts. Notably, this is the first coupling of ethanol with alkenes generating stereochemically enriched products. While the diastereoselectivity and yields are moderate to good, the regioselectivity of the reaction (1:2) is highly dependent on the nature of the diene substituent (R). This method accesses neopentyl ­homoallylic alcohols from inexpensive precursors through a non-obvious disconnection.

Review: J. F. Bower, I. S. Kim, R. L. Patman, M. J. Krische Angew. Chem. Int. Ed. 2009, 48, 34-46.