Direct asymmetric synthesis of δ-hydroxy-β-ketoesters
was accomplished via regio- and enantioselective aldol reactions of
β-ketoesters with isatins catalyzed by cinchona alkaloid thiourea
derivatives. The C–C bond formation of the reactions occurred
only at the γ-position of the β-ketoesters. Reaction progress
monitoring and product stability analyses under the conditions that
included the catalyst indicated that the γ-position reaction
products were formed kinetically. Various δ-hydroxy-β-ketoesters
bearing 3-alkyl-3-hydroxyoxindole cores relevant to the development
of bioactive molecules were synthesized.
[3 + 2] annulations of spirocyclopropyl oxindoles with ynamides to offer biologically important spirocyclopenteneoxindoles in high yields with good diastereoselectivities were developed.
1,3-Cyclohexandione derived cyclic ketals and thiol ketals were used as O- and S-nucleophiles, respectively for the ring opening of donor-acceptor cyclopropanes catalyzed by Cu(OTf)2 and a series of functionalized alkylene...
1,6-Dicarbonyl
compounds, representing the formal addition products
of the α-position of acetophenone derivatives to donor–acceptor
cyclopropanes, were synthesized in two steps via first ring opening
of donor–acceptor cyclopropanes with acyclic 1,3-diketones
followed by DBU catalyzed retro-Claisen-type C–C bond cleavage
reactions. In the first step, acyclic 1,3-diketones selectively worked
as C-nucleophiles to add to donor–acceptor cyclopropanes. In
the second step, the alkyl ketone part of the ring-opening products
resulting from unsymmetrical 1,3-diketones was selectively cleaved
in the presence of DBU in methanol.
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