ChemInform Abstract: Organocatalytic Asymmetric Michael Addition of 3‐Pyrrolyloxindoles to β‐Phthalimidonitroethene for the Synthesis of 3,3′‐Disubstituted Oxindoles Bearing Contiguous 3,α,β‐Triamino Functionality.

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An organocatalytic asymmetric Michael addition reaction of 3-pyrrolyloxindoles to β-phthalimidonitroethene has been developed with a bifunctional thiourea–tertiary amine as the catalyst. A range of 3,3′-disubstituted oxindoles bearing contiguous 3,α,β-triamino functionality could be obtained in high yields with good diastereoselectivities and high enantioselectivities (up to 99% yield, 99:1 dr, and 98% ee). The higher reactivity of β-phthalimidonitroethene compared to the reactivity of ordinary nitroalkenes in the reaction with 3-pyrrolyloxindoles was demonstrated by contrast experiments.