Abstract
One of the most efficient and reliable approaches to construct C–C bonds involves the conjugate addition of carbon nucleophiles to electron-deficient ketones. Yet, 1,6-conjugate additions of extended conjugated systems largely remain underexplored due to difficulties in controlling the regioselectivity. Herein, we report umpolung aldehydes as carbanion equivalents for highly regioselective 1,6-conjugate addition reactions to unsaturated ketones, with preliminary studies of the enantioselective variant. The synergy of ruthenium(ii) catalyst and electron-rich, bidentate phosphine ligand is essential for the reactivity and selectivity under mild reaction conditions.
Highlights
Building molecular complexity via C–C bond formations is an invaluable tool in synthetic chemistry and o en plays a pivotal role in reaction designs.[1]
The synergy of ruthenium(II) catalyst and electron-rich, bidentate phosphine ligand is essential for the reactivity and selectivity under mild reaction conditions
With our group's continuous pursuit in the umpolung of hydrazones as “so ” alkyl carbanions (Fig. 1b), we report the rst example of ruthenium-catalyzed 1,6-addition of hydrazones as a simple and effective nucleophile with excellent regioselectivity (Fig. 1c)
Summary
Building molecular complexity via C–C bond formations is an invaluable tool in synthetic chemistry and o en plays a pivotal role in reaction designs.[1]. Ruthenium(II)-catalyzed regioselective 1,6conjugate addition of umpolung aldehydes as carbanion equivalents† We report umpolung aldehydes as carbanion equivalents for highly regioselective 1,6-conjugate addition reactions to unsaturated ketones, with preliminary studies of the enantioselective variant.
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