Enantioselective cycloadditions of 2-alkenoylpyridine-N-oxides catalysed by a bis(oxazoline)/Cu~(II) complex: Structure of the reactive intermediate

Livieri A.; Boiocchi M.; Desimoni G.; Faita G.

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Enantioselective cycloadditions of 2-alkenoylpyridine-N-oxides catalysed by a bis(oxazoline)/Cu~(II) complex: Structure of the reactive intermediate

机译：由双（恶唑啉）/ Cu〜（II）复合物催化的2-链烯酰基吡啶-N-氧化物的映选择性环加成：反应性中间体的结构

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Diels-Alder and 1,3-dipolar cycloadditions involving (E)-3-aryl-1-(pyridin- 2-yl-N-oxide)prop-2-en-1-ones as the 2π components are efficiently catalysed by bis(oxazoline)-Cu~(II) complexes. The cycloadducts are obtained in quantitative yields with up to 98% ee; absolute configurations were determined by X-ray analysis. The structure of the reactive complex, determined by X-ray analysis, is fully consistent with the stereochemical outcome of the catalysed process (approach of the diene or nitrone to the less hindered face of the coordinated pyridine-N-oxide derivative).

机译：Diels-alder和1,3-偶极环加法涉及（e）-3-芳基-1-（吡啶-2-基-n-氧化物）prop-2-en-1-作为2π组分的促进剂（E）是有效的（恶唑啉）-cu〜（ii）复合物。在最高98％EE的定量产率下获得环形加法; 通过X射线分析确定绝对配置。通过X射线分析确定的反应性复合物的结构与催化过程的立体化学结果完全一致（二烯或亚硝基的方法，以与配位的吡啶-N-X氧化物衍生物的不太受阻面）完全一致。

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来源
《Chemistry: A European journal》 |2011年第2期|共5页
作者
Livieri A.; Boiocchi M.; Desimoni G.; Faita G.;
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作者单位

Department of Organic Chemistry University of Pavia V.le Taramelli 10 27100 Pavia Italy;

Centro Grandi Strumenti University of Pavia v. Bassi 8 27100 Pavia Italy;

Department of Organic Chemistry University of Pavia V.le Taramelli 10 27100 Pavia Italy;

Department of Organic Chemistry University of Pavia V.le Taramelli 10 27100 Pavia Italy;

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正文语种 eng
中图分类应用化学;
关键词
asymmetric catalysis; copper; cycloaddition; nitrogen heterocycles;

机译：不对称催化;铜;环加成;氮杂环;

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1. Enantioselective cycloadditions of 2-alkenoylpyridine-N-oxides catalysed by a bis(oxazoline)/Cu~(II) complex: Structure of the reactive intermediate [J] . Livieri A., Boiocchi M., Desimoni G., Chemistry: A European journal . 2011,第2期

机译：由双（恶唑啉）/ Cu〜（II）复合物催化的2-链烯酰基吡啶-N-氧化物的映选择性环加成：反应性中间体的结构
2. Enantioselective Friedel-Crafts alkylation of indoles with nitroalkenes catalyzed by a bis(oxazoline)-Cu(II) complex [J] . Pradeep K.Singh, Alakesh Bisai, Vinod K.Singh Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry . 2007,第7期

机译：双（恶唑啉）-Cu（II）配合物催化硝基苯与吲哚的对映选择性Friedel-Crafts烷基化反应
3. Catalytic highly enantioselective 1,3-dipolar cycloaddition reaction of nitrones with 3-alkenoyl-2-oxazolidinones by use of a bidentate chiral bis(imine)ligand-Cu(II)triflate complex [J] . Takao Saito, Takuya Yamada, Shingo Miyazaki, Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry . 2004,第52期

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4. Synthesis of Simple C2-Symmetric Chiral Bis(oxazoline)palladium(II) Complexes and Their Visualization of Reactivity [C] . Yuya Iwagoe, Daisetsu Yamanaka, Sei Matsunaga Symposium on Organometallic Chemistry . 2007

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5. I. Synthesis, reactivity, and structural studies of rhodium(III) and rhodium(II) complexes of novel bis(oxazoline) pincer ligands. II. Synthesis and reactivity of novel rhenium methylidene complexes. [D] . Krumper, Jennifer. 2003

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6. Chiral Bis(Imidazolidine)Pyridine-Cu Complex-Catalyzed Enantioselective 3+2-Cycloaddition of Azomethine Imineswith Propiolates [O] . Takayoshi Arai, Yuta Ogino 2012

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7. Enantioselective Addition of Activated Terminal Alkynes to 1-Acylpyridinium Salts Catalyzed by Cu-Bis(oxazoline) Complexes [O] . -1

机译：通过Cu-BIS（恶唑啉）络合物催化活化末端炔烃的激活末端醇盐加入1-酰基吡啶鎓盐

Enantioselective cycloadditions of 2-alkenoylpyridine-N-oxides catalysed by a bis(oxazoline)/Cu~(II) complex: Structure of the reactive intermediate

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