Combining Organocatalysis and Lanthanide Catalysis: A Sequential One-Pot Quadruple Reaction Sequence/Hetero-Diels–Alder Asymmetric Synthesis of Functionalized Tricycles
Dr. Simon Dochain
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany
Search for more papers by this authorM. Sc. Fabrizio Vetica
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany
Search for more papers by this authorDr. Rakesh Puttreddy
Department of Chemistry, Nanoscience Center, University of Jyvaskyla, 40014 JYU Finland
Search for more papers by this authorProf. Dr. Kari Rissanen
Department of Chemistry, Nanoscience Center, University of Jyvaskyla, 40014 JYU Finland
Search for more papers by this authorCorresponding Author
Prof. Dr. Dieter Enders
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany
Search for more papers by this authorDr. Simon Dochain
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany
Search for more papers by this authorM. Sc. Fabrizio Vetica
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany
Search for more papers by this authorDr. Rakesh Puttreddy
Department of Chemistry, Nanoscience Center, University of Jyvaskyla, 40014 JYU Finland
Search for more papers by this authorProf. Dr. Kari Rissanen
Department of Chemistry, Nanoscience Center, University of Jyvaskyla, 40014 JYU Finland
Search for more papers by this authorCorresponding Author
Prof. Dr. Dieter Enders
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany
Search for more papers by this authorGraphical Abstract
Targeting complexity: A unique combination of organocatalysis with lanthanide catalysis directly leads to complex tricyclic structures from readily available and simple compounds. Six new bonds and six stereocenters are formed with virtually complete stereoselectivity in this multicomponent one-pot procedure. fod=2,2-dimethyl-6,6,7,7,8,8,8-heptafluorooctane-3,5-dionato.
Abstract
A stereoselective one-pot synthesis of functionalized complex tricyclic polyethers has been achieved using the combination of secondary amine and lanthanide catalysis. This one-pot quadruple reaction/Hetero-Diels–Alder sequence gave good yields (per step) as well as excellent diastereo- and enantioselectivities. Furthermore, the particular combination of lanthanide complexes with organocatalysis is one of the first examples described for sequential catalysis.
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