Stereoselective Reduction of β-Hydroxy Ketones to 1, 3-Diols with the Aid of a Terphenyboronic Acid

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著者

    • YAMASHITA Hiroshi
    • Department of Chemistry, Graduate School of Science, The University of Tokyo
    • NARASAKA Koichi
    • Department of Chemistry, Graduate School of Science, The University of Tokyo

抄録

1-Hydroxy-6,8-diphenyl-1,2,3,4-tetrahydro-2-oxa-1-boranaphthalene (terphenylboronic acid <B>1</B>), is employed for stereoselective reduction of acyclic and cyclic <I>β</I>-hydroxy ketones. The terphenylboronic acid <B>1</B> and acyclic <I>β</I>-hydroxy ketones <B>2</B> are converted to the corresponding boronates by azeotropic removal of water. The resulting boronates are treated <I>in situ</I> with reducing reagents to give <I>syn</I> 1,3-diols <B>3</B> almost exclusively. <I>Anti</I> <I>α</I>-substituted <I>β</I>-hydroxy ketones <B>8</B> are also reduced to give <I>anti</I>, <I>anti</I> 1,3-diol <B>9</B> stereoselectively. Furthermore, the reduction of 3-hydroxy-1-cyclopentanone gives a <I>cis</I> diol <B>11</B> in high selectivity.

収録刊行物

  • Chemistry letters

    Chemistry letters 1996(7), 539-540, 1996-07

    The Chemical Society of Japan

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各種コード

  • NII論文ID(NAID)
    10002604481
  • NII書誌ID(NCID)
    AA00603318
  • 本文言語コード
    ENG
  • 資料種別
    ART
  • ISSN
    03667022
  • データ提供元
    CJP書誌  J-STAGE 
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