TY - JOUR A1 - Möhlmann, Lennart A1 - Chang, G.-H. A1 - Reddy, G. M. A1 - Lee, C.-J. A1 - Lin, W. T1 - Organocatalytic Enantioselective Synthesis of Tetrahydrofluoren-9- ones via Vinylogous Michael Addition/Henry Reaction Cascade of 1,3-Indandione-Derived Pronucleophiles N2 - An unprecedented organocatalytic enantioselective vinylogous Michael addition/Henry cyclization cascade is presented for the synthesis of highly substituted tetrahydrofluoren-9-ones 3 employing novel 1,3-indandionederived pronucleophiles 1a−g and nitroalkenes 2. Following a very simple protocol, a wide range of products were obtained in good to excellent yields and with excellent enantioinduction (43−98% yield, up to 98% ee). The reaction proceeded with excellent diastereocontrol despite the simultaneous generation of four stereogenic centers. Surprisingly, when 2-(1-phenylethylidene)-1H-indandione (1h) was used as a pronucleophile, no cyclization was observed, and only Michael addition adducts 4a−x were furnished in very good yields and excellent enantioselectivities. KW - square amide KW - organocatalysis KW - cascade reaction KW - enatioselective PY - 2016 U6 - https://doi.org/10.1021/acs.orglett.5b03663 SP - 688 EP - 691 AN - OPUS4-36952 LA - eng AD - Bundesanstalt fuer Materialforschung und -pruefung (BAM), Berlin, Germany ER -