Titanium(IV) Chloride‐Mediated Stereoselective α‐Alkylidenation to Efficiently Assemble Multisubstituted 1,3‐Dienes

作者: Rengwei Sun , Wei Song , Chunmei Ma , Huiwen Zhang , Xinhong Yu

DOI: 10.1002/ADSC.201601025

关键词:

摘要: A direct access to multisubstituted 1,3-dienes by α-exclusive alkylidenation of crotonic derivatives has been developed. This protocol, mediated titanium tetrachloride chelation, features excellent regio- and stereoselectivity, mild reaction conditions, easy operation wide substrate scope. Conversions the derived dienes other useful molecules were also explored.

参考文章(59)
R. S. Mali, S. G. Tilve, Convenient Synthesis of 2-Vinylindoles Synthetic Communications. ,vol. 20, pp. 2041- 2047 ,(1990) , 10.1080/00397919008053135
R. W. Dugger, Clayton H. Heathcock, A general synthesis of 5,6-dihydro-.alpha.-pyrones Journal of Organic Chemistry. ,vol. 45, pp. 1181- 1185 ,(1980) , 10.1021/JO01295A002
Bruce Irwin Rosen, William P. Weber, Electrocyclic synthesis of 5,6- and 7,8-dihydroquinolines and 5,6- and 7,8-dihydroisoquinolines Journal of Organic Chemistry. ,vol. 42, pp. 47- 50 ,(1977) , 10.1021/JO00421A010
K. C. Nicolaou, Scott A. Snyder, Tamsyn Montagnon, Georgios E. Vassilikogiannakis, Die Diels-Alder-Reaktion in der Totalsynthese Angewandte Chemie. ,vol. 114, pp. 1742- 1773 ,(2002) , 10.1002/1521-3757(20020517)114:10<1742::AID-ANGE1742>3.0.CO;2-Y
Michael W. Rathke, Donald Sullivan, The preparation and reactions of enolate anions derived from α,β-unsaturated esters Tetrahedron Letters. ,vol. 13, pp. 4249- 4252 ,(1972) , 10.1016/S0040-4039(01)94287-X
Xin-Fang Duan, Jing Zeng, Zhan-Bin Zhang, Guo-Fu Zi, A Facile Two-Step Synthesis of 2-Arylbenzofurans Based on the Selective Cross McMurry Couplings Journal of Organic Chemistry. ,vol. 72, pp. 10283- 10286 ,(2007) , 10.1021/JO7019652
Subramaniyan Mannathan, Chien-Hong Cheng, None, Cobalt-catalyzed regio- and stereoselective intermolecular enyne coupling: an efficient route to 1,3-diene derivatives Chemical Communications. ,vol. 46, pp. 1923- 1925 ,(2010) , 10.1039/B920071A
Akira Kajikawa, Masuo Morisaki, Nobuo Ikekawa, Exclusive γ-coupling in the aldol reaction of α,β-unsaturated esters Tetrahedron Letters. ,vol. 16, pp. 4135- 4136 ,(1975) , 10.1016/S0040-4039(00)91194-8