Synthesis 2017; 49(07): 1538-1546
DOI: 10.1055/s-0036-1588113
paper
© Georg Thieme Verlag Stuttgart · New York

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

Arne R. Philipps
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany   Email: enders@rwth-aachen.de
,
Marcus Blümel
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany   Email: enders@rwth-aachen.de
,
Simon Dochain
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany   Email: enders@rwth-aachen.de
,
Daniel Hack
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany   Email: enders@rwth-aachen.de
,
Dieter Enders*
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany   Email: enders@rwth-aachen.de
› Author Affiliations
Further Information

Publication History

Received: 09 November 2016

Accepted after revision: 11 November 2016

Publication Date:
06 December 2016 (online)


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.

Supporting Information

 
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