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Applications Of α-and β-Silylvinyl Grignard Reagents In Highly Selective Synthetic Reactions

Posted on:2007-11-25Degree:MasterType:Thesis
Country:ChinaCandidate:Z ZhouFull Text:PDF
GTID:2121360185972704Subject:Organic Chemistry
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In this dissertation we studied (Z)-α-silylvinyl Grignard reagents and (E)-α-iodovinylstannanes underwent a cross-coupling reaction in the presence of Pd(PPh3)4 catalyst to afford stereoselectively the difunctionalized 1,3-dienes containing silicon ang tin in good yields.We also studied the application of (E)-β-silylvinyl Grignard reagents in highly selective synthetic reactions. According to the literature procedure, (E)-β-silylvinyl Grignard reagents were prepared by hydromagnesiation of 1-aryl-2-silylacetylenes.We provided a facile route stereoselective synthesis of (2E)-3-silyl substituted allylic alcohols by the reaction of (E)-β-silylvinyl Grignard reagents with aldehydes or ketones. We also studied the reaction of (E)-β-silylvinyl Grignard reagents with trialkylstannyl chlorides in diethyl ether, which provided a new method for the stereoselective synthesis of (E)-β-silylvinylstannanes.
Keywords/Search Tags:hydromagnesiation, Grignard reagents, stereoselective synthesis, cross-coupling reaction, palladium catalysis, (E)-α-iodovinylstannane, silylarylacetylene, (E)-allylic alcohol, (E)-β-silylvinylstannane
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