Synthesis of E-α,β-unsaturated ketones with complete stereoselectivity via sequential aldol-type/elimination reactions promoted by samarium diiodide or chromium dichloride

被引:21
|
作者
Concellón, JM [1 ]
Rodríguez-Solla, H [1 ]
Concellón, C [1 ]
Díaz, P [1 ]
机构
[1] Univ Oviedo, Dipartimento Quim Organ & Inorgan, E-33006 Oviedo, Spain
关键词
alkenes; chromium; diastereoselectivity; samarium; ketones; sequential reactions;
D O I
10.1055/s-2006-933146
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
E-alpha,beta-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 SmI2, SmI2 in the presence of FeCl3 or CrCl2. The best results were obtained when CrCl2 was used as the metallating agent. A mechanism based on a successive aldol-type reaction and a beta-elimination is proposed to explain these results.
引用
收藏
页码:837 / 840
页数:4
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