Enantioselective Synthesis of Tertiary Propargylic Alcohols under N-Heterocyclic Carbene Catalysis

Sanchez-Diez Eduardo; Fernandez Maitane; Uria Uxue; Reyes Efraim; Carrillo Luisa; Vicario Jose L.

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Enantioselective Synthesis of Tertiary Propargylic Alcohols under N-Heterocyclic Carbene Catalysis

机译：N-杂环碳烯催化下对丙炔醇的对映选择性合成

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A straightforward procedure to carry out the enantioselective benzoin reaction between aldehydes and ynones by employing a chiral N-heterocyclic carbene (NHC) as catalyst was developed. Under the optimized reaction conditions, these ynones undergo a clean and selective 1,2-addition with the catalytically generated Breslow intermediate, not observing any byproduct arising from competitive Stetter-type reactivity. This procedure allows the preparation of tertiary alkynyl carbinols as highly enantioenriched materials, which have the remarkable potential to be used as chiral building blocks in organic synthesis.

机译：通过使用手性N-杂环卡宾（NHC）作为催化剂，开发了一种简单的方法来进行醛和炔酮之间的对映选择性安息香反应。在优化的反应条件下，这些炔酮与催化生成的Breslow中间体进行了清洁，选择性的1,2-加成反应，未观察到任何由竞争性Stetter型反应性产生的副产物。该方法允许将叔炔基甲醇制备为高度对映体富集的材料，其具有用作有机合成中的手性结构单元的显着潜力。

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《Chemistry: A European journal》 |2015年第23期|共5页
作者
Sanchez-Diez Eduardo; Fernandez Maitane; Uria Uxue; Reyes Efraim; Carrillo Luisa; Vicario Jose L.;
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正文语种 eng
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关键词
alkynes; asymmetric catalysis; carbenes; organocatalysis; umpolung;

机译：炔烃;不对称催化;卡宾;有机催化;化学计量;

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1. Enantioselective Synthesis of Tertiary Propargylic Alcohols under N-Heterocyclic Carbene Catalysis [J] . Sanchez-Diez Eduardo, Fernandez Maitane, Uria Uxue, Chemistry: A European journal . 2015,第23期

机译：N-杂环碳烯催化下对丙炔醇的对映选择性合成
2. Synthesis of N-Heterocyclic Carbene Complexes of Manganese(I)by Coupling Isocyanide Ligands with Propargylamines and Propargylic Alcohols [J] . Javier Ruiz, Bernabe F.Perandones, Gabriel Garcia Organometallics . 2007,第23期

机译：异氰化物配体与炔丙基胺和炔丙基醇的偶联反应合成锰（I）N-杂环碳配合物
3. Highly Enantioselective Synthesis of Functionalized Glutarimide Using Oxidative N-Heterocyclic Carbene Catalysis: A Formal Synthesis of (-)-Paroxetine [J] . Porey Arka, Santra Surojit, Guin Joyram The Journal of Organic Chemistry . 2019,第9期

机译：使用氧化N-杂环催化催化芳丙基甲酰胺的高映射合成：（ - ） - 帕罗西汀的正式合成
4. N-Heterocyclic Carbene Ligands Bearing Hydrophilic and/or Hydrophobic Chains:The Design,Synthesis and Catalysis [C] . Hidetoshi Ohta, Tetsuaki Fujihara, Yasushi Tsuji Symposium on Organometallic Chemistry . 2007

机译：载有亲水性和/或疏水链的N-杂环配体：设计，合成和催化
5. Catalytic enantioselective synthesis of tertiary propargylic alcohols: Al-catalyzed asymmetric alkylation of pyridyl-ynones with dialkylzinc reagents [D] . Friel, Donna Kay 2008

机译：叔炔丙醇的催化对映选择性合成：用二烷基锌试剂进行铝催化的吡啶基炔酮的不对称烷基化
6. Catalytic Nucleophilic Fluorination of Secondary and Tertiary Propargylic Electrophiles with a Copper–N-Heterocyclic Carbene Complex [O] . Li-Jie Cheng, Christopher J Cordier -1

机译：铜-N-杂环碳烯络合物对仲和叔丙炔亲电子的催化亲核氟化
7. Versatile relay and cooperative palladium(0) N-heterocyclic carbene/copper(I) N-heterocyclic carbene catalysis for the synthesis of tri- and tetrasubstituted alkenes [O] . Lesieur, Mathieu, Bidal, Yannick Daniel, Lazreg, Faima, 2015

机译：多功能中继和协作钯（0）N-杂环卡宾/铜（I）N-杂环卡宾催化合成三和四取代烯烃

Enantioselective Synthesis of Tertiary Propargylic Alcohols under N-Heterocyclic Carbene Catalysis

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