Cyclo- and hydrodimerization of α,β-unsaturated ketones promoted by samarium diiodide

被引:44
作者
Cabrera, A
Le Lagadec, R
Sharma, P
Arias, JL
Toscano, RA
Velasco, L
Gaviño, R
Alvarez, C
Salmón, M
机构
[1] Univ Nacl Autonoma Mexico, Inst Quim, Mexico City 04720, DF, Mexico
[2] Univ Nacl Autonoma Mexico, Fac Estudios Super, Estado De Mexico, Mexico
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1998年 / 21期
关键词
D O I
10.1039/a804269a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Samarium(II) iodide is a strong one-electron transfer reducing agent, and is effective for the cyclo- and hydrodimerization of cyclic and non-cyclic alpha,beta-unsaturated ketones. The title dimers can easily be prepared in good yields at room temperature under neutral conditions, using two-mole equivalent of SmI2 per mole of starting substrate. The reaction is stereocontrolled. The absence of an alcohol as a proton source is essential in the process and the use of HMPA as a copromoter improves the yield of dimeric products, making the reaction regioselective over the competitive C=C double bond reduction. The crystal structures of some of the dimeric derivatives are reported. When eta(2)- or eta(4)-iron-coordinated alpha,beta-unsaturated ketones are used as substrates, the reaction gives mainly the 1,4-reduced products.
引用
收藏
页码:3609 / 3617
页数:9
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