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Synfacts 2010(8): 0926-0926  
DOI: 10.1055/s-0030-1257780
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

C-C Coupling of Ethanol and Dienes

Contributor(s): Mark Lautens, Jane Panteleev
H. Han, M. J. Krische*
University of Texas at Austin, USA
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Publication History

Publication Date:
22 July 2010 (online)

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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.