Mild, Efficient, and Robust Method for Stereocomplementary Iron-Catalyzed Cross-Coupling Using (E)- and (Z)-Enol Tosylates

[摘要]：Iron-catalyzed cross-coupling of Grignard reagents (RMgX) with (E)- and (Z)-enol tosylates proceeded smoothly to give a variety of the corresponding (E)-and (Z)-trisubstituted alpha,beta-bunsaturated methyl esters (total 30 examples; 55-98% yield). The simple, mild, stereoretentive method utilized iron(III) chloride (FeCl3), iron(III) acetylacetonate [Fe(acac)(3)], and iron(III) tris(dibenzylmethane) [Fe(dbm)(3)]. The (E)-and (Z)-enol tosylates were readily prepared by the reported stereocomplementary tosylation method from methyl beta-keto esters or alpha-formyl esters. Methyl alpha-formyl esters were obtained via a practical and robust TiCl4-Et3N-mediated alpha-formylation of methyl esters with methyl formate.

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