N-Heterocyclic Carbene Catalyzed Reaction of 2-(2-Aroylvinyl)cinnamalde­hydes with α,β-Unsaturated Imines: An Efficient Method for the Stereoselective Synthesis of Highly Functionalized Indane Derivatives

Abstract

The NHC-catalyzed reaction of 2-(2-aroylvinyl)cinnamaldehydes with α,β-unsaturated imines was studied, which produced­ good yields of novel 3-aryl-9-[1,3-diaryl-3-(4-tolylsulfonamido)allyl]-9,9a-dihydroindeno[2,1-c]pyran-1(4aH)-ones with high diastereoselectivity. The products can be easily converted into different highly functionalized indane derivatives via simple operations. Thus, this work provides a simple and efficient method for the stereoselective synthesis of 1,2,3-trisubstituted indane derivatives.

Key words

N-heterocyclic carbene - catalysis - 2-(2-aroylvinyl)cinnamaldehyde - α,β-unsaturated imine - indane

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