Sequential Elimination-Reduction Reactions Promoted by Samarium Diiodide: Synthesis of 2,3-Dideuterioesters or -amides

Jose M. Concellon; Humberto Rodriguez-Solla

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Sequential Elimination-Reduction Reactions Promoted by Samarium Diiodide: Synthesis of 2,3-Dideuterioesters or -amides

机译：二碘化Sa促进的顺序消除-还原反应：2,3-二异丁酸酯或-酰胺的合成

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A facile and general sequential elimination/reduction process promoted by samarium diiodide provides an efficient method for synthesizing saturated esters or amides 3 from readily available starting materials. The reaction involves a #beta#-elimination of the starting 2-halo-3-hydroxyesters or -amides 1 and subsequent 1,4-reduction of the obtained #alpha#,#beta#-unsaturated esters or amides in the presence of H_2O. When D_2O is used instead of H_2O, 2,3-dideuterioesters or -amides 4 are isolated. A mechanism is proposed to account for this synthesis.

机译：由二碘化promote促进的简便且通用的顺序消除/还原过程提供了一种从容易获得的起始原料合成饱和酯或酰胺3的有效方法。该反应涉及在H_2O存在下＃β＃消除起始的2-卤代-3-羟基酯或-酰胺1，随后1,4-还原所得的＃α＃，＃β＃-不饱和酯或酰胺。。当使用D_2O代替H_2O时，分离出2,3-二异丁酸酯或-酰胺4。提出了一种机制来解释这种综合。

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《Chemistry: A European journal》 |2001年第19期|共6页
作者
Jose M. Concellon; Humberto Rodriguez-Solla;
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原文格式 PDF
正文语种 eng
中图分类化学;应用化学;
关键词
deuterium; elimination; reduction; samarium; sequential reactions;

机译：氘消除还原mar顺序反应;

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1. Sequential Elimination-Reduction Reactions Promoted by Samarium Diiodide: Synthesis of 2,3-Dideuterioesters or -amides [J] . Jose M. Concellon, Humberto Rodriguez-Solla Chemistry: A European journal . 2001,第19期

机译：二碘化Sa促进的顺序消除-还原反应：2,3-二异丁酸酯或-酰胺的合成
2. Synthesis of E-alpha,beta-unsaturated ketones with complete stereoselectivity via sequential aldol-type/elimination reactions promoted by samarium diiodide or chromium dichloride [J] . Concellon JM, Rodriguez-Solla H, Concellon C, Synlett . 2006,第6期

机译：通过二碘化sa或二氯化铬促进的连续羟醛型/消除反应合成具有完全立体选择性的E-α，β-不饱和酮
3. An Easy,Efficient,and Completely Stereoselective Synthesis of (E)-alpha,beta-Unsaturated Esters via Sequential Aldol-Type/Elimination Reactions Promoted by Samarium Diiodide or Chromium Dichloride [J] . Jose M.Concellon, Carmen Concellon, Carmen Mejica The Journal of Organic Chemistry . 2005,第15期

机译：通过二碘化mar或二氯化铬促进的顺序Aldol-类型/消除反应轻松，高效和完全立体选择性地合成（E）-α，β-不饱和酯
4. Coupling Reaction Between (Haloarene)Tricarbonylchromium Complexes and Benzylic Halides, Mediated by Samarium Diiodide [C] . E. Parlea, S. Rosca, J.L. Namy 12th Romanian International Conference on Chemistry and Chemical Engineering Sep 13-15, 2001 Bucharest, Romania . 2001

机译：二碘化Sa介导的（卤代芳烃）三羰基铬配合物与卤代苯的偶联反应
5. Samarium diiodide-mediated tandem radical-ionic reactions: Model studies towards the total synthesis of penitrem D. [D] . Rivkin, Alexey. 2001

机译：di二碘化物介导的串联自由基离子反应：对Penitrem D进行全合成的模型研究。
6. Preparation and Use of Samarium Diiodide (SmI2) in Organic Synthesis: The Mechanistic Role of HMPA and Ni(II) Salts in the Samarium Barbier Reaction [O] . Dhandapani V. Sadasivam, Kimberly A. Choquette, Robert A. Flowers II 2013

机译：二碘化mar（SmI2）的制备及其在有机合成中的应用：HMPA和Ni（II）盐在BarBarbier反应中的机理作用
7. An Easy, Efficient, and Completely Stereoselective Synthesis of (E)-α,β-Unsaturated Esters via Sequential Aldol-Type/Elimination Reactions Promoted by Samarium Diiodide or Chromium Dichloride. [O] . Jose M. Concellon, Carmen Concellon, Carmen Mejica 2005

机译：通过钐亚硫化物或二氯化铬促进的顺序醛醇型/消除反应，通过序贯的醛醇型/消除反应容易，高效，完全立体化合成（E）-α，β-不饱和酯。

Sequential Elimination-Reduction Reactions Promoted by Samarium Diiodide: Synthesis of 2,3-Dideuterioesters or -amides

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