Categories: C-O Bond Formation > Synthesis of alcohols (hydroxylation) >
Synthesis of allyl alcohols
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Recent Literature
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.
C. Morrill, R. H. Grubbs, J. Am. Chem. Soc.,
2005,
127, 2842-2843.
C. Morrill, R. H. Grubbs, J. Am. Chem. Soc.,
2005,
127, 2842-2843.
Gold N-heterocyclic carbene complexes, in conjunction with a
silver salt, were found to efficiently catalyze the rearrangement of allylic
acetates under both conventional and microwave-assisted heating. The steric hindrance of
the ligand bound to gold was found crucial as
only extremely bulky ligands permitted the isomerization.
N. Marion, R. Gealageas, S. P. Nolan, Org. Lett., 2007,
9, 2653-2656.
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