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

来源：

SYNLETT | 2006年 / 06期

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

页码：837 / 840

页数：4

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