Enzyme-catalyzed enantioselective and regioselective hydrolyses of (2RS, 7SR)-2,7-diacetoxybicyclo(2.2.1)heptane and (2RS, 7RS)-2,7-diacetoxybicyclo(2.2.1)heptane.

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概要

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• Enzyme-catalyzed hydrolyses of (2<I>RS</I>,7<I>SR</I>)-2,7-diacetoxybicyclo[2.2.1]heptane (<B>2</B>) and its (2<I>RS</I>,7<I>RS</I>)-isomer <B>6</B> occurred with regiospecificity combined with enantiomeric specificity to give the diacetates and the monoacetates in optically active forms, and the acetoxyl group located on the methano bridge in the diacetates was preferentially hydrolyzed to give the monoacetates. Treatment with lithium aluminum hydride converted (−)-<B>2</B> and (+)-(2<I>S</I>,7<I>R</I>)-2-acetoxybicyclo[2.2.1]heptan-7-ol into (+)-(2<I>R</I>,7<I>S</I>)-bicyclo[2.2.1]heptane-2,7-diol (<B>1</B>) and (−)-(2<I>S</I>,7<I>R</I>)-bicyclo[2.2.1]heptane-2,7-diol (<B>1</B>), respectively, from which both enantiomers of <B>1</B> with <I>≥</I>98% e.e. were readily obtained by further recrystallization. Similarly, (−)-(2<I>R</I>,7<I>R</I>)-2,7-diacetoxybicyclo[2.2.1]heptane (<B>6</B>) and (+)-(2<I>S</I>,7<I>S</I>)-2-acetoxybicyclo[2.2.1]heptan-7-ol (<B>6</B>) were converted into (+)-(2<I>R</I>,7<I>R</I>)-bicyclo[2.2.1]heptane-2,7-diol (<B>5</B>) and (−)-(2<I>S</I>,7<I>S</I>)-bicyclo[2.2.1]heptane-2,7-diol (<B>5</B>), respectively. The absolute configurations of the products were determined by a chemical correlation with <I>exo</I>-2-acetoxybicyclo[2.2.1]heptane of known absolute configuration.

• 公益社団法人 日本化学会の論文

著者

• Naemura Koichiro

  Department Of Chemistry Faculty Of Engineering Science Osaka University

• Takahashi Nobuo

  Department Of Applied Biochemistry Hiroshima University

• Tanaka Shunsuke

  Department Of Chemical Engineering Faculty Of Engineering Kansai University

• Chikamatsu Hiroaki

  Department Of Chemistry Faculty Of Engineering Science Osaka University

• Ueno Michi

  Department of Chemistry, Faculty of Engineering Science, Osaka University

• Tanaka Shunsuke

  Department of Chemistry, Faculty of Engineering Science, Osaka University

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