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Study On The Synthesis Of 1, 5-Benzodiazepines And Steroeselective Synthesis Of Heterocyclic α-Amino Phosphonates Catalyzed By Lanthanide Compounds

Posted on:2009-03-29Degree:MasterType:Thesis
Country:ChinaCandidate:S E FengFull Text:PDF
GTID:2121360245460521Subject:Organic Chemistry
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The lanthanide compounds catalyzed synthesis of 1,5-benzodiazepines and stereoselective synthesis of heterocyclicα-amino phosphonates are studied in this thesis, which is composed with three parts as follows:1. A series of 1,5-benzodiazepines were efficiently synthesized by the reaction of o-phenylenediamine andα,β-unsaturated ketones catalyzed by ytterbium chloride. The reaction was carried out under mild conditions and gave the products in moderate to excellent yields.2. The reaction of 1,5-benzodiazepine and diethyl phosphite catalyzed by in-situ formed chiral lanthanide complex was studied, and the influence of the catalyst composition and reaction conditions on the reactivity and enatioselectivity was investigated. The reaction afforded the heterocyclicα-amino phosphonate in high yield with enantiomeric excesses up to 66%.3. The diastereoselectivity of the lanthanide compounds catalyzed one-pot reaction of o-phenylenediamine,α,β-unsaturated ketones and dialkyl phosphites was explored.
Keywords/Search Tags:1,5-benzodiazepine, lanthanide chloride, ytterbium chloride, catalysis, synthesis, α-amino phosphonate, tris(bis(trimethylsilyl)amino)lanthanum, Binol, stereoselectivity
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