A Facile Zn-mediated Stereoselective Synthesis of (E)- and (Z)-Trisubstituted Alkenes from Baylis-Hillman Adducts in Water and Its Application

この論文にアクセスする

この論文をさがす

著者

    • DAS Biswanath
    • Organic Chemistry Division-I, Indian Institute of Chemical Technology
    • MAJHI Anjoy
    • Organic Chemistry Division-I, Indian Institute of Chemical Technology
    • MAHENDER Gurram
    • Organic Chemistry Division-I, Indian Institute of Chemical Technology

抄録

A simple and efficient stereoselective synthesis of (<I>E</I>)- and (<I>Z</I>)-trisubstituted alkenes has been accomplished by treatment of the acetyl derivatives of the Baylis–Hillman adducts with Zn in saturated aq. NH<SUB>4</SUB>Cl solution under reflux. The method has been utilized for the preparation of the two chiral insect pheromones, dominicalure-I and dominicalure-II, of the lesser grain borer <I>Rhyzopertha dominica</I> (F).

収録刊行物

  • Chemistry letters

    Chemistry letters 35(4), 358-359, 2006-04-05

    The Chemical Society of Japan

参考文献:  21件中 1-21件 を表示

  • <no title>

    BAYLIS A. B.

    German Patent 2155113, 1972

    被引用文献1件

  • <no title>

    HOFFMAN H. M. R.

    Angew. Chem., Int. Ed. Engl. 24, 94, 1985

    被引用文献1件

  • <no title>

    WILLIAM H. J.

    J. Chem. Ecol. 7, 759, 1981

    被引用文献1件

  • <no title>

    LIN-YU L.

    J. Chem. Ecol. 16, 1921, 1990

    被引用文献1件

  • <no title>

    HOFFMANN H. M. R.

    J. Org. Chem. 50, 3849, 1985

    被引用文献1件

  • <no title>

    BASAVAIAH D.

    J. Org. Chem. 64, 1197, 1999

    被引用文献1件

  • <no title>

    FERNANDES L.

    Tetrahedron 60, 9983, 2004

    被引用文献1件

  • <no title>

    LI J.

    Tetrahedron Lett. 46, 1931, 2005

    被引用文献1件

  • <no title>

    LI J.

    Tetrahedron 60, 5793, 2004

    被引用文献1件

  • <no title>

    LI C.-J. ed.

    Organic Reactions in Aqueous Media, 1997

    被引用文献1件

  • <no title>

    GRIECO P. A. ed.

    Organic Synthesis in Water, 1998

    被引用文献1件

  • <no title>

    DAS B.

    Org. Lett. 6, 3349, 2004

    被引用文献1件

  • <no title>

    BASAVAIAH D.

    Chem. Rev. 103, 811, 2003

    被引用文献13件

  • <no title>

    BUCHHOLZ R.

    Helv. Chim. Acta 74, 1213, 1991

    被引用文献7件

  • Multicomponent alarm pheromones in the weaver ant

    BRADSHAW J. W. S.

    Nature 258, 230-231, 1975

    被引用文献2件

  • <no title>

    ROSSI R.

    Tetrahedron 48, 8801-8824, 1992

    被引用文献3件

  • The biosynthesis of marine natural-products

    GARSON M. J.

    Chem. Rev. 93, 1699-1733, 1993

    被引用文献2件

  • <no title>

    MARFORT A.

    J. Org. Chem. 44, 3888, 1979

    被引用文献1件

  • <no title>

    PACHAMUTHU K.

    Tetrahedron Lett. 39, 5439, 1998

    被引用文献1件

  • <no title>

    SHADAKSHARI U.

    Tetrahedron 57, 4599, 2001

    DOI 被引用文献1件

  • <no title>

    AMRI H.

    Tetrahedron 46, 3535, 1990

    被引用文献1件

被引用文献:  1件中 1-1件 を表示

各種コード

  • NII論文ID(NAID)
    10018125155
  • NII書誌ID(NCID)
    AA00603318
  • 本文言語コード
    ENG
  • 資料種別
    SHO
  • ISSN
    03667022
  • データ提供元
    CJP書誌  CJP引用  J-STAGE 
ページトップへ