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Study Of Asymmetric Reduction Of Phenylethanolamines The Key Intermediates Of β-receptor Agonists

Posted on:2012-06-30Degree:MasterType:Thesis
Country:ChinaCandidate:G XiaoFull Text:PDF
GTID:2211330368998830Subject:Organic Chemistry
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α-Halo-acetophenone derivatives was asymmetricly catalyzed by using catalysts (R/S)-α,α-diphenyl-2-pyrrolidinemethanol,(1R,2S)-2-Amino-1,2- diphenylethanol,(R)-a,a-diphenyl-2- pyrrolidinemethanol and (+/-)Diiso- pinocampheylchloroboranend to obtain a Series of chiralα-halo secondary alcohols the key intermediates ofβ-receptor agonists were studies in this thesis ,and this thesis is divided into three parts as follows:The first part is about synthesis of prochiral ketones.α-halo-acetophenone derivatives containα-chlor-acetophenones what are synthsised by friedel-crafts reaction andα-brom-acetophenones what are synthsised by Acetophenone directly reacting with bromide.The second part is about synthesis of (+/-)-Diisopinocampheyl- chloroborane what is synthsised from (-/+)-α-Pinene and study of redution activity ofα-halo-acetophenone derivatives by using (+/-)-DiisopinocampheylchloroboraneThe third part is about synthesis of ((1S,2R)/(1R,2S))-(-)-2-Amino-1,2- diphenylethanol what is synthsised through benzoic conden-sation then reacting with hydroxylamine hydrochloride and catalyzed reducting by Pd/C and amine borane complexes what are important part of CBS redutive reaction and can be synthsised by amine reacting with BH3 or Borane-tetrahydrofuran complex.At last it is about study of activity of the three catalysts (R/S)-α,α-diphenyl-2-pyrrolidinemethanol,(1R,2S)-2-Amino-1,2-diphenylethanol,(R)-a,a-diphenyl-2-pyrrolidinemethanol and the reductive activity of amine borane complexes in CBS catalytic redution.
Keywords/Search Tags:CBS catalytic redution, α-halo secondary alcohols, amine borane complexes, intermediates ofβ-receptor agonists
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