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The Synthesis Of Phosphoryl Coumarins And The Design/synthesis Of Chiral Organocatalyst And Its Application In Asymmetric Synthesis

Posted on:2008-02-26Degree:MasterType:Thesis
Country:ChinaCandidate:L WangFull Text:PDF
GTID:2121360215965830Subject:Analytical Chemistry
Abstract/Summary:PDF Full Text Request
A series of coumarins were phosphorylated with diisopropylphophite (DIPPH) and diethylphosphite (DEPPH) by Atherton-Todd reaction in 64-96% yields successfully, and the coumarin derivatives with high pharmaceutical value were obtained by chemical modification. A number of aldehydes react with acetic anhydride in the presence of catalytic amount of beta zeolite to afford the corresponding 1, 1-diacetates in good to excellent yields. The beta zeolite has showed high catalytic activity in this reaction. L-(+)-Tartaric acid is used as starting material to synthesize a serial of chiral tetraphenyl diols which can be used as the ligands in the asymmetric catalysis reactions. (1S, 2S)-(-)-1, 2-Diphenylethylene-Diamine is synthesized from benzaldehyde in 6 steps, the method is simple and reliable and the yield is high. Homochiral (1S, 2S)-(-)-1, 2-Diphenylethylene-Diamine was used as the start material to synthesize a series of chiral bifunctional thioureas with reactive function groups and try to use them to catalyze the Michael addition of secondary amine such as pyrrolidine to 2(5H)-furanone . Chiral bifunctional thiourea with Schiff base was found to have good solubility and proper catalytic groups; it is very promising to asymmetrically catalyze the Michael addition of secondary amine toα,β-unsarurated lactones. Via the researching work of this dissertation, new notion has been put forward to asymmetrically catalyze the Michael addition ofα,β-unsarurated lactones. Thismakes it possible to mimic the enzymes.
Keywords/Search Tags:phosphorylation, coumarin, diacetates, organocatalysis, thiourea
PDF Full Text Request
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