Rapid Construction Of The N-Spiro-azabiindane Skeleton

Currently,chiral ligand promoted asymmetric reaction is a hot issue and a frontier of the research in organic chemistry,the design and synthesis of chiral ligands with novel skeletons and the applications in new reactions are the focus of asymmetric reactions.During the last three decades,ligands with spiro skeletons received increasing attention and considerable development,which has resulted in a broad application in the synthesis of chiral compounds.In this thesis,the first preparation of N-chiral quaternary ammonium salts possessing a N-spiro-azabiindane skeleton has been achieved in synthetically useful yield from readily available compounds.This novel N-spiro-azabiindane skeleton was constructed by phenolic hydroxyl allylation,Claisen rearrangement,ozonization reaction,reductive amination reaction,and intramolecular SNAr reaction.The N-spiro-azabiindane skeleton was further confirmed by the transformation of the compounds with non C2 symmetric skeleton to that with C2 symmetric structure.The construction of this new N-spiro-azabiindane skeleton paves the base for the development of new chiral spiro ligands and new chiral catalysts.