A nickel-catalyzed cross-coupling of alkenyl methyl ethers with Grignard reagents, under mild conditions, is described. These conditions allowed access to various stilbenes and heterocyclic stilbenic derivatives as well as to a potential anticancer agent DMU-212.
The synthesis of various optically active α-trifluoromethylamines has been realized from β-amino-α-trifluoromethyl alcohols via an aziridinium ion intermediate under kinetic conditions.
Cyclopropane fusion of the only rotatable
carbon–carbon
bond in furanosyl nucleosides (i.e., exocyclic 4′–5′)
is a powerful design strategy to arrive at conformationally constrained
analogues. Herein, we report a direct stereodivergent route toward
the synthesis of the four possible configurations of 4-spirocyclopropane
furanoses, which have been transformed into the corresponding 4′-spirocyclic
adenosine analogues. The latter showed differential inhibition of
the protein methyltransferase PRMT5-MEP50 complex, with one analogue
inhibiting more effectively than adenosine itself, demonstrating the
utility of rationally probing 4′–5′ side chain
orientations.
4-Aminopropargylic acetates afford 4-amino-1-allenylsilanes upon reaction with the lithium (triorganosilyl)zincate (PhMe2Si)3ZnLi. The reaction is both stereoselective and stereospecific and proceeds through syn-silylzincation of the carbon–carbon triple bond followed by subsequent anti-β-elimination of the acetate group.
The synthesis of cyclopropyl pinacol boronic esters from dibromocyclopropanes via Matteson–Pasto rearrangement is reported. The method is readily scalable and shows limited levels of stereoinduction, with a selectivity that is in part complementary to that observed in existing stereoselective borylcyclopropanation strategies. The method can be used to rapidly access borylcyclopropanes as interesting building blocks for diversely functionalized cyclopropanes.
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