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Stereoselective Preparation of (E)-α-Bromoacrylates from Mixtures of Brominated Ando Phosphonates

Thomas Olpp, Reinhard Brückner*

*Institut für Organische Chemie und Biochemie, Albert-Ludwigs-Universität, Albertstr. 21, 79104 Freiburg, Germany, Email:

T. Olpp, R. Brückner, Synthesis, 2004, 2135-2152.

DOI: 10.1055/s-2004-831166


Deprotonation of a 64:36 mixture of ethyl bromo(diphenylphosphono)acetate and ethyl dibromo(diphenylphosphono)acetate using NaH as base at 0 °C and subsequent reaction with various aldehydes provided unsaturated α-bromoesters in good yields and high E-selectivities.

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Key Words

α-bromoacrylates, alkenyl halides, α-chloroacrylates, Horner-Wadsworth-Emmons olefination, α,β-unsaturated esters

ID: J66-Y2004-2290