Synthesis of chiral biphenol-based diphosphonite ligands and their application in palladium-catalyzed intermolecular asymmetric allylic amination reactions.
A library of new 2,2'-bis(diphenylphosphinoyloxy)-1,1'-binaphthyl (binapo)-type chiral diphosphonite ligands was designed and synthesized based on chiral 3,3',5,5',6,6'-hexasubstituted biphenols. These bop ligands have exhibited excellent efficiency in a palladium-catalyzed intermolecular allylic amination reaction, which provides a key intermediate for the total synthesis of Strychnos indole alkaloids with enantiopurities of up to 96% ee.
Department of Chemistry, State University of New York at Stony Brook, Stony Brook, New York 11794-3400, USA.
Ce
C
Shi
Chih-Wei
CW
Chien
Iwao
I
Ojima
D000498:Allyl Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D000586:Amination; D002384:Catalysis; D026121:Indole Alkaloids / Q000138:chemical synthesis; D009943:Organophosphorus Compounds / Q000138:chemical synthesis / Q000737:chemistry; D010165:Palladium / Q000737:chemistry*; D010636:Phenols / Q000138:chemical synthesis / Q000737:chemistry*; D031451:Strychnos / Q000737:chemistry
D000498:Allyl Compounds; D026121:Indole Alkaloids; D009943:Organophosphorus Compounds; D010636:Phenols; D010165:Palladium