The First Example of Enantioselective Protonation of Prochiral Enolates with Chiral γ-Hydroxyselenoxides

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著者

    • TAKAHASHI Tamiko
    • Faculty of Pharmaceutical Sciences, Toyama Medical & Pharmaceutical University
    • NAKAO Naoki
    • Faculty of Pharmaceutical Sciences, Toyama Medical & Pharmaceutical University
    • KOIZUMI Toru
    • Faculty of Pharmaceutical Sciences, Toyama Medical & Pharmaceutical University

抄録

Enantioselective protonation of a simple enolate has been developed using an optically pure γ-hydroxyselenoxide <B>1</B> as a chiral proton source. Reaction of zinc bromide enolate <B>7b</B> with (<I>S</I><SUB>Se</SUB>)-selenoxide (<I><B>S</B></I><SUB><B>Se</B></SUB>)-<B>1c</B> gave (<I>S</I>)-2-benzylcyclohexanone <B>(<I>S</I>)-8</B> with high enantioselectivity. Intramolecular hydrogen bonding between hydroxy group and seleninyl-oxygen of <B>1</B> would contribute to this asymmetric induction.

収録刊行物

  • Chemistry letters

    Chemistry letters 1996(3), 207-208, 1996-03-05

    The Chemical Society of Japan

参考文献:  11件中 1-11件 を表示

  • <no title>

    MORRISON J. D.

    Asymmetric Synthesis 2, 1983

    被引用文献1件

  • <no title>

    MORRISON J. D.

    Asymmetric Synthesis 3, 1984

    被引用文献1件

  • <no title>

    KOMATSU N.

    Synth. Org. Chem. 53, 268, 1995

    被引用文献1件

  • <no title>

    TAKAHASHI T.

    J. Org. Chem. 59, 3262, 1994

    被引用文献4件

  • <no title>

    MEYERS A. I.

    J. Am. Chem. Soc. 103, 3081, 1981

    被引用文献3件

  • <no title>

    MATSUMOTO K.

    Tetrahedron Lett. 32, 4729, 1991

    被引用文献2件

  • <no title>

    AUERBACH R. A.

    Organic Syntheses VI, 692, 1988

    被引用文献1件

  • <no title>

    MEYERS A. I.

    J. Am. Chem. Soc. 98, 3032, 1976

    被引用文献1件

  • <no title>

    HOSHINO K.

    The Book of Abstracts of 20th Symposium on Heteroatom Chemistry, Tokyo 5, 1993

    被引用文献1件

  • <no title>

    KOSUGI H.

    The Book of Abstracts of 22nd Symposium on Heteroatom Chemistry, Nagoya 93, 1995

    被引用文献1件

  • <no title>

    YANAGISAWA A.

    Synlett 1995, 372

    被引用文献1件

各種コード

  • NII論文ID(NAID)
    10003739071
  • 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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