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The Study Of Ring-Opening Allylation Of Epoxides In Aqueous Media

Posted on:2005-05-15Degree:MasterType:Thesis
Country:ChinaCandidate:Y F HanFull Text:PDF
GTID:2121360125466360Subject:Organic Chemistry
Abstract/Summary:PDF Full Text Request
1. Study on the ring-opening allylation of terminal epoxides in aqueous mediaThe ring-opening allylation of terminal epoxides mediated by indium, tin, and zinc metal under various conditions, such as under aqueous conditions and sonicate condition without solvent, was investigated. The ring-opening allylation of terminal epoxides mediated by SnCl2 with Cu, KI, or CuCl2 under aqueous condition at different pH values was also investigated.2. Research on the Synthesis of a novel chiral catalyst (4R)-benzyloxy- (S)-proline and catalytic direct asymmetryic aldol reactions(4R)-hydroxy-(S)-proline was N-protected by the reaction with di-tert-butyl pyrocarbonate to give N-Boc-(4R)-hydroxy-(S)-proline, which was treated with NaH in anhydrous tetrahydrofuran and followed by etherification with PhCH2Br to form the N-Boc-(4R)-benzyloxy-(S)-proline, which, after removal of the protecting group with CF3COOH, gave the title compound This compound can serve as an efficient catalyst for the direct asymmetryic aldol reaction with the yield ranged from 58% to 91% and up to 89.3% enantiomeric excess. We also studied the asymmetryic aldol reactions catalyzed by the peptides of H-L-Pro-L-Pro-OH and H-L-Pro-D-Pro-OH.
Keywords/Search Tags:ring opening, allylation, proline, asymmetric, aldol reaction, catalyst
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