Synthesis of E-α, β-unsaturated ketones with complete stereoselectivity via sequential aldol-type/elimination reactions promoted by samarium diiodide or chromium …
JM Concellón, H Rodríguez-Solla, C Concellón…
Index: Concellon, Jose M.; Rodriguez-Solla, Humberto; Concellon, Carmen; Diaz, Pamela Synlett, 2006 , # 6 p. 837 - 840
Full Text: HTML
Citation Number: 5
Abstract
Abstract E-α, β-Unsaturated ketones can be obtained with complete E-selectivity by a sequential reaction of dichloroketones with a variety of aldehydes. This transformation was promoted by SmI 2, SmI 2 in the presence of FeCl 3 or CrCl 2. The best results were obtained when CrCl 2 was used as the metallating agent. A mechanism based on a successive aldol-type reaction and a β-elimination is proposed to explain these results.
Related Articles:
[Wang, Xinliang; Liu, Renhua; Jin, Yu; Liang, Xinmiao Chemistry - A European Journal, 2008 , vol. 14, # 9 p. 2679 - 2685]
[Heshmatpour, Felora; Abazari, Reza; Balalaie, Saeed Tetrahedron, 2012 , vol. 68, # 14 p. 3001 - 3011]
[Shen, Shu-Su; Kartika, Vita; Tan, Ying Shan; Webster, Richard D.; Narasaka, Koichi Tetrahedron Letters, 2012 , vol. 53, # 8 p. 986 - 990]
Palladated Kaiser oxime resin as precatalyst for the Heck reaction in organic and aqueous media
[Synlett, , # 18 p. 2959 - 2964]
[Heshmatpour, Felora; Abazari, Reza; Balalaie, Saeed Tetrahedron, 2012 , vol. 68, # 14 p. 3001 - 3011]