Stereochemical studies on the nucleophilic substitution in the reaction of allylic phosphates with organoaluminum reagents.

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概要

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• The reaction of <I>cis</I>- or <I>trans</I>-5-isopropenyl-2-methyl-2-cyclohexenyl diethyl phosphate (<B>1</B>) with Me<SUB>2</SUB>AlX (X=OPh, SPh, NHPh) in hexane results in substitution of the –O–PO(OEt)<SUB>2</SUB> group with X under predominant inversion. In contrast, treatment of <I>cis</I>- or <I>trans</I>-<B>1</B> with trialkylaluminum produces predominantly the allyl-nonallyl couplingproducts of the same (thermodynamically more stable) configuration. Similar alkylation of <I>endo</I>- and <I>exo</I>-2-acetoxynorcarane gave <I>endo</I>-2-methylnorcarane, exclusively.

• 公益社団法人 日本化学会の論文

著者

• YAMAMOTO Hajime

  Department of Applied Physics and Chemistry, The University of Electro-Communications

• Hiyama Tamejiro

  Department Of Marerial Chemistry Graduate School Of Engineering Kyoto University

• Oshima Koichiro

  Department Of Industrial Chemistry Faculty Of Engineering Kyoto University

• Nozaki Hitosi

  Department of Industrial Chemistry, Faculty of Engineering Kyoto University

• Itoh Akira

  Department of Applied Chemistry, Faculty of Engineering, Osaka University

• Ozawa Shuji

  Department of Industrial Chemistry, Faculty of Engineering, Kyoto University

• Sasaki Shizuka

  Department of Industrial Chemistry, Faculty of Engineering, Kyoto University

• Oshima Koichiro

  Department of Chemistry, Massachusetts Institute of Technology

• Hiyama Tamejiro

  Department of Industrial Chemistry, Faculty of Engineering, Kyoto University

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