Synthesis of Enantioenriched 5,6-Dihydrophenanthridine Derivatives through retro-Carbopalladation of Chiral o-Bromobenzylamines†
Dr. Juntao Ye
Davenport Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, ON, M5S 3H6 (Canada)
Search for more papers by this authorAurore Limouni
Davenport Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, ON, M5S 3H6 (Canada)
Search for more papers by this authorSonia Zaichuk
Davenport Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, ON, M5S 3H6 (Canada)
Search for more papers by this authorCorresponding Author
Prof. Dr. Mark Lautens
Davenport Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, ON, M5S 3H6 (Canada)
Davenport Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, ON, M5S 3H6 (Canada)Search for more papers by this authorDr. Juntao Ye
Davenport Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, ON, M5S 3H6 (Canada)
Search for more papers by this authorAurore Limouni
Davenport Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, ON, M5S 3H6 (Canada)
Search for more papers by this authorSonia Zaichuk
Davenport Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, ON, M5S 3H6 (Canada)
Search for more papers by this authorCorresponding Author
Prof. Dr. Mark Lautens
Davenport Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, ON, M5S 3H6 (Canada)
Davenport Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, ON, M5S 3H6 (Canada)Search for more papers by this authorWe thank the Natural Sciences and Engineering Research Council (NSERC), the University of Toronto, and Alphora Research Inc for financial support. M.L. thanks the Canada Council for the Arts for a Killam Fellowship. Dr. Alan Lough (Department of Chemistry, University of Toronto) is acknowledged for X-ray analysis. We also thank D. Petrone and Dr. L. Zhang from our group for helpful discussions.
Abstract
Retro-carbopalladation of aldimines in the presence of a suitable β-hydrogen atom has been observed in the Pd-catalyzed homocoupling reactions of o-bromobenzylamines, providing an expeditious synthetic route to 5,6-dihydrophenanthridine derivatives. Furthermore, a highly enantioselective synthesis of 6-aryl-substituted 5,6-dihydrophenanthridines was achieved in a one-pot manner by taking advantage of Rh and Pd catalysis.
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