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Silica gel-promoted synthesis of multisubstituted spiroindolenines from tryptamines and γ-chloro-α,β-unsaturated ketones

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ABSTRACT Here we report a one-pot synthesis of multisubstituted spiroindolenines from a series of tryptamine derivatives with γ-chloro-α,β-unsaturated ketones. The reaction sequence consists of base-induced condensation and silica gel-promoted intramolecular… Click to show full abstract

ABSTRACT Here we report a one-pot synthesis of multisubstituted spiroindolenines from a series of tryptamine derivatives with γ-chloro-α,β-unsaturated ketones. The reaction sequence consists of base-induced condensation and silica gel-promoted intramolecular Michael addition. The target molecules are afforded in up to 90% yield with up to >20:1 diastereoselectivity.

Keywords: unsaturated ketones; synthesis multisubstituted; multisubstituted spiroindolenines; chloro unsaturated; silica gel; gel promoted

Journal Title: Tetrahedron
Year Published: 2021

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