Synthesis of Chiral Tertiary Amine–Thioureas Based on Spirobi­indane and Application in Catalytic Asymmetric Michael Addition Reaction

Abstract

A series of novel chiral bifunctional tertiary amine–thioureas based on spirobiindane were designed and synthesized as organo­catalysts. One of these catalysts was shown to promote the asymmetric Michael addition reaction of 1,3-diphenylpropane-1,3-dione to nitro­olefins, affording the desired products in good yields (up to 95%) and enantioselectivities (up to 98% ee).

Key words

organocatalysis - Michael addition - nitroolefins - spiro skeleton - thiourea

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