π-アリルパラジウム錯体の見かけ上の電荷反転 : アリルアルコール類によるカルボニル-アリル化反応への応用
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概要
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Palladium-catalyzed carbonyl allylation by allylic alcohols with SnCl<SUB>2</SUB> smoothly proceeds in aqueous medium under air. The actual allylating agent in the carbonyl allylation by allyl alcohol in dry medium is allyltrichlorotin, which is prepared via (1) oxidative addition of allyl alcohol to Pd (0) complex with SnCl<SUB>2</SUB>, (2) insertion of SnCl<SUB>2</SUB> to π-allylpalladium complex, followed by (3) reductive elimination of π-allylpalladium trichlorostannate. Allylic alcohols, preparing π-allylpalladium complexes, function as synthons of allylic carbanions. In other words, this implies the apparent charge reversal of electrophilic π-allylpalladium complexes. The carbonyl allylation by allylic alcohols can achieve high chemo-, regio-, and diastereoselection by the choice of solvent, and can be applied to chelation-controlled diastereoselection in polar solvents.
- 社団法人 有機合成化学協会の論文
著者
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増山 芳郎
上智大学理工学部化学科
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Masuyama Yoshiro
Research Laboratory of Resources Utilization, Tokyo Institute of Technology
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- π-アリルパラジウム錯体の見かけ上の電荷反転 : アリルアルコール類によるカルボニル-アリル化反応への応用
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