Categories: Synthesis of O-Heterocycles >
Synthesis of 2H-pyran-5-ones
Recent Literature
Synthetic transformations of the products of the Achmatowicz rearrangement
with potassium organotrifluoroborates in the absence of transition metals
provide dihydropyranones (2,6-trans), tetrahydropyranones (2,3-cis-2,6-cis) or
functionalized 1,4-dicarbonyl compounds depending on the reaction conditions and
the substitution pattern. The method has also been adapted for the one-pot
synthesis of functionalized pyrroles.
S. Roscales, V. Ortega, A. G. Csák˙, J. Org. Chem., 2018, 83,
11425-11436.
A Pd-catalyzed arylation of Achmatowicz rearrangement products with
arylboronic acids provides synthetically versatile C-aryl dihydropyranones under
mild conditions.
M. W. Liaw, W. F. Cheng, R. Tong, J. Org. Chem., 2020, 85,
6663-6674.
Lipase B from Candida antarctica catalyzes the oxidative ring expansion of
furfuryl alcohols in the presence of aqueous hydrogen peroxide to yield
functionalized pyranones under mild conditions. The corresponding piperidinone
derivatives can be obtained by a similar enzymatic rearrangement of N-protected
furfurylamines.
F. Blume, P. Sprengart, J. Deska,
Synlett, 2018, 29, 1293-1296.
