An enantioselective catalytic approach to syn deoxypropionate units combining asymmetric Cu-catalyzed 1, 6-and 1, 4-conjugate addition

T den Hartog, DJ van Dijken, AJ Minnaard…

Index: Den Hartog, Tim; Jan Van Dijken, Derk; Minnaard, Adriaan J.; Feringa, Ben L. Tetrahedron Asymmetry, 2010 , vol. 21, # 11-12 p. 1574 - 1584

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Citation Number: 24

Abstract

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- ...