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Research On Asymmetric Organocatalysis

Posted on:2010-02-14Degree:MasterType:Thesis
Country:ChinaCandidate:J YangFull Text:PDF
GTID:2121360275958840Subject:Organic Chemistry
Abstract/Summary:PDF Full Text Request
Part 1: Highly Diastereo- and Enantioselective Organocatalytic Addition of Acetone toβ-Substitutedα-Ketoesters via Dynamic Kinetic ResolutionThe L-proline catalyzed aldol reactions ofβ-substitutedα-ketoester with acetone proceeded with dynamic kinetic resolution and gave a single diastereoisomer in good yield with excellent diastereoselectivity (dr up to >99:1) and enantioselectivity (ee up to 98%). The absolute configuration of the chiral adduct was assigned by a single crystal X-ray diffraction analysis. A tentativel reaction mechanism was briefly discussed.Part 2: Design of Tunable Bifunctional Organocatalyst Based on Molecular Recognition and its application in Asymmetric Michael Addition Reaction of Ketones to NitroolefinsA new catalyst was designed based on molecular recognition. Its application in asymmetry Michael addition reaction was investigated. The possible dual activation model was proposed.
Keywords/Search Tags:Aldol Reaction, Dynamic Kinetic Resolution, β-Substitutedα-Ketoester, Michael Addition, Bifunctional Organocatalyst, Molecular Recognition, Organocatalysis
PDF Full Text Request
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