Enantioselective Catalytic One-Pot Synthesis of Functionalized Methyleneindanes and Methylindenes via a Michael/Conia-Ene Sequence

Abstract

An enantioselective one-pot Michael addition/Conia-ene reaction sequence catalyzed by the combination of a squaramide and indium(III) triflate has been developed. Employing 2-ethynyl-β-nitrostyrenes and 1,3-dicarbonyl compounds as substrates, the functionalized methyleneindanes and methylindenes are obtained in good to excellent enantiomeric excesses. For the indane/indene conversion a concerted fragmentation is proposed.

Key words

organocatalysis - indium catalysis - Conia-ene reaction - indanes - indenes

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