Cinchona-derived Amines Research Articles

Regio- and Diastereodivergent [4 + 2] Cycloadditions with Cyclic 2,4-Dienones.

By employing activated alkenes with bulky α-functional groups, such as α-cyano-α,β-unsaturated ketones and Meldrum's acid-based alkenes, a previously unreported cross-trienamine pathway of cyclic 2,4-dienones is adopted to deliver γ',δ-regioselective [4 + 2] cycloadducts catalyzed by cinchona-derived amines. In addition, a diastereodivergent [4 + 2] cycloaddition reaction is realized with Z-configured 4-alkylideneisoxazol-5(4H)-ones under similar catalytic conditions, even through a three- or four-component cascade process with simple starting materials.

ChemInform Abstract: α‐Regioselective [3 + 2] Annulations with Morita—Baylis—Hillman Carbonates of Isatins and 2‐Nitro‐1,3‐enynes.

An α-regioselective asymmetric [3 + 2] annulation reaction with Morita–Baylis–Hillman carbonates of isatins and (E)-2-nitro-1,3-enynes catalysed by cinchona-derived amines has been developed, providing spirooxindoles with contiguous chiral centres including adjacent quaternary ones in moderate to good yields with high enantioselectivity and excellent diastereoselectivity.

α-Regioselective [3 + 2] annulations with Morita–Baylis–Hillman carbonates of isatins and 2-nitro-1,3-enynes

An α-regioselective asymmetric [3 + 2] annulation reaction with Morita–Baylis–Hillman carbonates of isatins and (E)-2-nitro-1,3-enynes catalysed by cinchona-derived amines has been developed.