Benzofulvenes in Trienamine Catalysis: Stereoselective Spiroindene Synthesis
Bjarke S. Donslund
Department of Chemistry, Aarhus University, Langelandsgade 140, 8000 Aarhus C, Denmark
Search for more papers by this authorRune Pagh Nielsen
Department of Chemistry, Aarhus University, Langelandsgade 140, 8000 Aarhus C, Denmark
Search for more papers by this authorSofie M. N. Mønsted
Department of Chemistry, Aarhus University, Langelandsgade 140, 8000 Aarhus C, Denmark
Search for more papers by this authorCorresponding Author
Prof. Karl Anker Jørgensen
Department of Chemistry, Aarhus University, Langelandsgade 140, 8000 Aarhus C, Denmark
Search for more papers by this authorBjarke S. Donslund
Department of Chemistry, Aarhus University, Langelandsgade 140, 8000 Aarhus C, Denmark
Search for more papers by this authorRune Pagh Nielsen
Department of Chemistry, Aarhus University, Langelandsgade 140, 8000 Aarhus C, Denmark
Search for more papers by this authorSofie M. N. Mønsted
Department of Chemistry, Aarhus University, Langelandsgade 140, 8000 Aarhus C, Denmark
Search for more papers by this authorCorresponding Author
Prof. Karl Anker Jørgensen
Department of Chemistry, Aarhus University, Langelandsgade 140, 8000 Aarhus C, Denmark
Search for more papers by this authorAbstract
The asymmetric formation of spiroindenes containing up to four contiguous stereocenters from the reaction of benzofulvenes with 2,4-dienals through trienamine catalysis is described. The benzofulvene core was found to be an excellent starting point for the synthesis of interesting spiroindenes through a formal cycloaddition pathway. The reaction was mediated by a diphenylprolinol silyl ether catalyst, and a diverse array of spiroindenes were obtained in high yields with excellent stereoselectivity. An attractive feature of the developed system is the possibility to diversify the product scaffold significantly by further manipulation of the chiral spiroindenes. Thus, three intramolecular ring-closing reactions following the organocatalytic step resulted in highly complex polycyclic systems.
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