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Highly Regio-, Diastereo-, and Enantioselective [2+2+2] Cycloaddition of 1,6-Enynes with Electron-Deficient Ketones Catalyzed by a Cationic RhI/H8-binap Complex

Authors

  • Ken Tanaka Prof. Dr.,

    1. Department of Applied Chemistry, Graduate School of Engineering, Tokyo University of Agriculture and Technology, Koganei, Tokyo 184-8588, Japan, Fax: (+81) 42-388-7037
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  • Yousuke Otake,

    1. Department of Applied Chemistry, Graduate School of Engineering, Tokyo University of Agriculture and Technology, Koganei, Tokyo 184-8588, Japan, Fax: (+81) 42-388-7037
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  • Hiromi Sagae,

    1. Department of Applied Chemistry, Graduate School of Engineering, Tokyo University of Agriculture and Technology, Koganei, Tokyo 184-8588, Japan, Fax: (+81) 42-388-7037
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  • Keiichi Noguchi Prof. Dr.,

    1. Instrumentation Analysis Center, Tokyo University of Agriculture and Technology, Koganei, Tokyo 184-8588, Japan
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  • Masao Hirano Dr.

    1. Department of Applied Chemistry, Graduate School of Engineering, Tokyo University of Agriculture and Technology, Koganei, Tokyo 184-8588, Japan, Fax: (+81) 42-388-7037
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  • This research was partly supported by a Grant-in-Aid for Scientific Research on Priority Areas (No. 19028015, Chemistry of Concerto Catalysis) from the Ministry of Education, Culture, Sports, Science and Technology (Japan). We thank Yusuke Aida (TUAT) for his experimental assistance and Takasago International Corporation for the gift of modified binap ligands. H8-binap=2,2′-bis(diphenylphosphanyl)-5,5′,6,6′,7,7′,8,8′-octahydro-1,1′-binaphthyl.

Abstract

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Zwei quartäre Kohlenstoffzentren entstehen bei der im Titel genannten Bildung von anellierten Dihydropyranen (siehe Schema). Der gleiche Katalysator vermittelt auch die ortho-Funktionalisierung von Arylketonen mit 1,6-Eninen mit ausgezeichneter Regio- und Enantioselektivität. Z=Amid, C(CO2Me)2, O; E=CO2Et, Ac; R1=Me, Aryl, CO2Me; R2=Me; R3=Me, CO2Et.

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