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

Hiroshi Nishikado, Hidefumi Nakatsuji, Kanako Ueno, Ryohei Nagase, Yoo Tanabe*

*Department of Chemistry, School of Science and Technology, Kwansei Gakuin University, 2-1 Gakuen, Sanda 669-1337, Japan, Email:

H. Nishikado, H. Nakatsuji, K. Ueno, R. Nagase, Y. Tanabe, Synlett, 2010, 2087-2092.

DOI: 10.1055/s-0030-1258131

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Iron-catalyzed cross-coupling of Grignard reagents with (E)- and (Z)-enol tosylates proceeded smoothly to give a variety of the corresponding (E)- and (Z)-trisubstituted α,β-unsaturated methyl esters in good yield. The simple, mild, stereoretentive method utilized iron(III) chloride and other iron salts as catalyst.

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General, Robust, and Stereocomplementary Preparation of α,β-Disubstituted α,β-Unsaturated Esters

H. Nakatsuji, H. Nishikado, K. Ueno, Y. Tanabe, Org. Lett., 2009, 11, 4258-4261.

Key Words

cross-coupling, iron, stereoselective synthesis, enol tosylates, α,β-unsaturated esters

ID: J60-Y2010-2370