Iron-catalyzed Stereoselective Allylboration Of 3,4-Dihydroisoquinoline

The application of iron-based compounds as catalysts in organic synthesis is extremely attractive because their prices are far lower than the frequently used precious metal catalysts.In recent years,the prices of many transition metals and rare earth metals have risen sharply,making it possible to find cheaper alternatives.It is imminent;in addition,various iron compounds are widely present in various organisms,so many iron compounds have relatively low toxicity to organisms,which is important for many modern synthetic manufacturing industries including the pharmaceutical industry,the food industry and the cosmetics industry.Has important value.The wide biological activities of isoquinoline alkaloids have attracted the attention of many chemical synthesis and medicine neighborhoods,and many related products have been widely used in clinical practice.Its synthesis,especially the synthesis of complex derivatives,often has problems such as many synthesis steps,expensive reaction materials and catalysts,and many by-products.The allyl boron reagent can react with carbonyl compounds or imines to obtain chiral alcohols and amines with complex structures with multiple chiral centers through a simple one-step reaction.It has important potential applications in the synthesis of quinolines and derivatives.The compound is used as a catalyst,and the allyl boron reagent is used to realize the synthesis of isoquinoline derivatives not only to meet the requirements of green chemistry,but also to achieve the purpose of simple steps and lower costs.This article is divided into two parts,introducing several allyl boron reagents and several isoquinoline synthesis methods,as well as the addition of allyl boron reagents to isoquinoline.Part Ⅰ: Prepare a series of dihydroisoquinolines with various substituent phenethylamines as starting materials,and prepare corresponding allyl boron reagents through several steps of reactions with several enols as raw materials.Synthesize 1-methyl-3,4-dihydroisoquinolines with various substituents on the benzene ring and other types of 3,4-dihydroisoquinolines,as well as several allyls with different alkyl substituents Allyl boron reagents such as potassium fluoroborate and chiral potassium fluoroborate.Part Ⅱ: Using several 3,4-dihydroisoquinoline and allyl boron reagents as substrates to study the iron-catalyzed allylation reaction of dihydroisoquinoline,a series of experiments were carried out to obtain suitable Based on the catalytic system and reaction conditions of the iron compound,study the application range of 3,4-dihydroisoquinoline and allyl boron reagent in the target catalytic system and the specific reaction conditions,explore the law of the target reaction,and based on this reaction Obtain a series of new compounds to obtain their precise structures.