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 (free Supporting Information)
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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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