1,1'-Binaphthyl-2,2'-diyl Phosphoroselenoyl Chloride as a Chiral Molecular Tool for the Preparation of Enantiomerically Pure Alcohols and Amines

摘要

The development of new tools,which can be used to determine the enantiomeric purities of a chiral substance,resolve chiral molecules,and promote asymmetric catalytic reactions,is of great importance in modern organic chemistry.Although various types of chiral discriminating agents have been developed,the analysis,resolution,and preparation of simple optically active secondary alcohols,found in a wide variety of biologically active natural compounds,such as insect pheromones,represent a continuing challenge in organic chemistry.As a result,new chiral molecular tools,which can be used not only as chiral derivatizing agents but also as chiral resolving agents,remain in high demand.Below,we report the preparation of l,l'-binaphthyl-2,2'-diyl phosphoroselenoyl chloride and describe its utility as a new chiral molecular tool to promote chiral discrimination and enantiomer resolution,as well as to mediate stereocontrolled amination reactions of simple secondary alcohols.