Organic Chemistry Portal

Abstracts

Search:

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: tanabekwansei.ac.jp

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

DOI: 10.1055/s-0030-1258131


see article for more reactions

Abstract

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.


see article for more examples



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