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Regio- and Stereocontrol in Rhenium-Catalyzed Transposition of Allylic Alcohols

Aaron T. Herrmann, Tatsuo Saito, Craig E. Stivala, Janine Tom and Armen Zakarian*

*Department of Chemistry and Biochemistry, University of California, Santa Barbara, California 93106-9510, Email: zakarianchem.ucsb.edu

A. T. Herrmann, T. Saito, C. E. Stivala, J. Tom, A. Zakarian, J. Am. Chem. Soc., 2010, 132, 5962-5963.

DOI: 10.1021/ja101673v (free Supporting Information)


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Abstract

A hydroxyl group-directed, highly regio- and stereoselective transposition of allylic alcohols based on rhenium catalysis is suitable for a direct isomerization of acetals into the thermodynamically preferred isomer as long as one of the hydroxyl groups is allylic. This method will expand the scope of rhenium-catalyzed alcohol transpositions for complex molecule synthesis.


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Key Words

allylic alcohols, isomerisation of alkenes, benzylidene acetals


ID: J48-Y2010-1210