Study On The Addition Reaction Of Potassium Allyl Fluoroborate To Imine And Aldehyde

Chiral alcohols and chiral amines are widely found in many natural products or synthetic drugs.They are favored by many chemists and medical scientists for their wide biological activity,and many drugs have been widely used in clinic.The synthesis of its complex,especially the synthesis of structurally complex molecules,often requires multiple reactions,and the problem of waste production is serious.Thanks to the development of synthetic science,organic boron reagents have been widely used in the synthesis of highly selective C-C bonds due to their low toxicity and stability.During the period,allyl boron reagents have received extensive attention due to their very specific activities and the simple reaction of carbonyl compounds or imines to obtain chiral alcohols and amines with complex structures in the achiral center.There are important potential applications in green chemistry.In this paper,two parts are introduced to study the addition reaction of two allyl boron reagents to imine and aldehyde.Part ?:Allyl addition of dihydroisoquinoline catalyzed by Fe.Tetrahydroisoquinoline and its derivatives are widely found in nature as a class of alkaloids.In this study,we found a suitable Fe catalyst,and used the allyl boron reagent to have reaction at the C=N bond of dihydroisoquinoline and introduced the allyl group at the 1-position,and obtained racemic chiral tetrahydroisoquinoline.The allyl moiety can further participate in many useful synthetic transformations,providing a new idea for the synthesis of natural products such as tetrahydroisoquinoline alkaloids and their derivatives.Part ?:Synthesis and isomer separation of cis-?,?-disubstituted-1,4-butyrolactone.As an important pharmaceutical intermediate,y-butyrolactone has been the focus of research.In this paper,chiral allyl boron reagent was added to aldehyde to synthesize y-butyrolactone in a green way in water.For the case where two isomers have been difficult to separate,silver nitrate-loaded method successfully separated it and obtained the target product with high enantioselectivity.