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

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  • Biswanath Das
    Organic Chemistry Division-I, Indian Institute of Chemical Technology
  • Nikhil Chowdhury
    Organic Chemistry Division-I, Indian Institute of Chemical Technology
  • Joydeep Banerjee
    Organic Chemistry Division-I, Indian Institute of Chemical Technology
  • Anjoy Majhi
    Organic Chemistry Division-I, Indian Institute of Chemical Technology
  • Gurram Mahender
    Organic Chemistry Division-I, Indian Institute of Chemical Technology

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Abstract

<jats:title>Abstract</jats:title> <jats:p>A simple and efficient stereoselective synthesis of (E)- and (Z)-trisubstituted alkenes has been accomplished by treatment of the acetyl derivatives of the Baylis–Hillman adducts with Zn in saturated aq. NH4Cl 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 Rhyzopertha dominica (F).</jats:p>

Journal

  • Chemistry Letters

    Chemistry Letters 35 (4), 358-359, 2006-03-11

    Oxford University Press (OUP)

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