1,3-Dipolar cycloadditions of cyclic nitrones to achiral and
chiral p-benzoquinone monoketals have
shown poor chemo- and stereoselectivity. To overcome these
problems, a highly efficient strategy
has been set up on the basis of the temporary conjugate addition of
thiophenol to the dipolarophile.
The phenylthio derivative 10b, available in both
enantiopure forms, has demonstrated to be effective
as a masked chiral synthetic equivalent of p-benzoquinone in
the model reaction.
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