1255649-69-4Relevant academic research and scientific papers
Mild, efficient, and robust method for stereocomplementary iron-catalyzed cross-coupling using (E)- and (Z)-enol tosylates
Nishikado, Hiroshi,Nakatsuji, Hidefumi,Ueno, Kanako,Nagase, Ryohei,Tanabe, Yoo
experimental part, p. 2087 - 2092 (2010/10/03)
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 ,-unsaturated 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). The (E)- and (Z)-enol tosylates were readily prepared by the reported stereocomplementary tosylation method from methyl -keto esters or -formyl esters. Methyl -formyl esters were obtained via a practical and robust TiCl4-Et3N-mediated -formylation of methyl esters with methyl formate.
