1246668-28-9Relevant academic research and scientific papers
An enantioselective catalytic approach to syn deoxypropionate units combining asymmetric Cu-catalyzed 1,6- and 1,4-conjugate addition
Den Hartog, Tim,Jan Van Dijken, Derk,Minnaard, Adriaan J.,Feringa, Ben L.
, p. 1574 - 1584 (2010)
A novel iterative approach to the synthesis of the naturally ubiquitous syn deoxypropionate motif is reported. The route comprises a new Horner-Wadsworth-Emmons reagent to prepare α,β,γ,δ- bisunsaturated thioesters. Next, two Me-substituents are introduced in high yield, regio- and enantioselectivity using sequential asymmetric Cu-catalyzed 1,6-conjugate addition, base-catalyzed olefin isomerization and Cu-catalyzed enantioselective 1,4-conjugate addition. After reduction to the aldehyde these transformations can be repeated to install three or more Me groups with a syn 1,3-relationship.
