Highly Selective 1,3-Isomerization of Allylic Alcohols via Rhenium Oxo Catalysis

Christie Morrill and Robert H. Grubbs*

*Arnold and Mabel Beckman Laboratory of Chemical Synthesis, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, Email: rhgcaltech.edu

C. Morrill, R. H. Grubbs, J. Am. Chem. Soc., 2005, 127, 2842-2843.

DOI: 10.1021/ja044054a

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Abstract

O₃ReOSiPh₃ promotes the 1,3-isomerization of various allylic alcohols. Two different strategies allow the selective formation of a single isomer. The first strategy utilizes the formation of a conjugated alkene to ensure a high selectivity. The second strategy employs N,O-bis(trimethylsilyl)acetamide (BSA) as an additive to remove the product from the reaction equilibrium and works well for the isomerization of tertiary allylic alcohols.

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Key Words

Isomerisation of alkenes, allyl alcohols

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ID: J48-Y2005-2270