Catalytic asymmetric electrophilic alpha-amination of alpha-cyanoketones in the presence of chiral palladium complexes

Lee JH; Bang HT; Kim DY

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Catalytic asymmetric electrophilic alpha-amination of alpha-cyanoketones in the presence of chiral palladium complexes

机译：手性钯配合物的催化不对称亲电α-氰基酮的α-氨基化

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摘要

The catalytic enantioselective electrophilic alpha-amination promoted by chiral palladium complexes is described. Treatment of alpha-cyanoketones with azodicarboxylates as electrophilic amination reagents under mild reaction conditions afforded the corresponding alpha-amino alpha-cyanoketones with excellent enantiomeric excesses (81-95% ee).

机译：描述了由手性钯配合物促进的催化对映选择性亲电子α-胺化。在温和的反应条件下，用偶氮二羧酸酯作为亲电胺化试剂处理α-氰基酮，得到相应的α-氨基α-氰基酮，其对映体过量极好（81-95％ee）。

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《Synlett》 |2008年第12期|共4页
作者
Lee JH; Bang HT; Kim DY;
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正文语种 eng
中图分类有机化学;
关键词
electrophilic amination; asymmetric catalysis; chiral palladium catalysts; alpha-cyanoketones; QUATERNARY AMMONIUM-SALTS; PHASE-TRANSFER CATALYSIS; AMINO-ACID DERIVATIVES; BETA-KETO-ESTERS; ENANTIOSELECTIVE FLUORINATION; NONADJACENT STEREOCENTERS; 1; 3-DICARBONYL COMPOUNDS; STRECKER REACTION; CYANO ACETATES; KETOESTERS;

机译：亲电胺化;不对称催化;手性钯催化剂;α-氰基酮;季铵盐;相转移催化;氨基酸衍生物;BETA-酮基酯;对映选择性氟化;不相邻的立体异构体;1;3-二聚体;Cyano乙酰乙酸盐;酮;

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专利

1. Catalytic asymmetric electrophilic alpha-amination of alpha-cyanoketones in the presence of chiral palladium complexes [J] . Lee JH, Bang HT, Kim DY Synlett . 2008,第12期

机译：手性钯配合物的催化不对称亲电α-氰基酮的α-氨基化
2. Catalytic Asymmetric Electrophilic ￥á-Amination of ￥a-Ketoesters in the Presence of Chiral Nickel Complexes [J] . Dae Gil Kwon, Dae Young Kim, Joo Yang Mang Bulletin of the Korean Chemical Society . 2009,第1期

机译：手性镍配合物存在下α-酮酸酯的催化不对称亲电子式￥á-胺化
3. Catalytic asymmetric Mannich-type reactions of fluorinated ketoesters with N-Boc aldimines in the presence of chiral palladium complexes [J] . Young Ku Kang, Dae Young Kim Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry . 2011,第18期

机译：手性钯配合物存在下氟化酮酯与N-Boc Aldimines的催化不对称曼尼希型反应
4. Direct Enolate Formation of Active Methylene Compounds Using Chiral Palladium Complexes:Catalytic Enantioselective Michael Reaction and Fluorination [C] . Yoshitaka Hamashima, Daido Hotta, Hisashi Takano, Symposium on Organometallic Chemistry . 2003

机译：使用手性钯配合物直接烯醇形成活性亚甲基化合物：催化对映选择性迈克尔反应和氟化
5. Synthesis and chemistry of iridium complexes containing chiral diphosphine ligands: Oxidative addition to iridium(I) systems and catalytic activity of the electrophilic iridium(III) complexes. [D] . Atesin, Abdurrahman Cagri. 2008

机译：含手性二膦配体的铱配合物的合成与化学：铱（I）系统的氧化加成和亲电铱（III）配合物的催化活性。
6. C2-Symmetric chiral bis(oxazoline)–metal complexes in catalytic asymmetric synthesis [O] . Arun K. Ghosh, Packiarajan Mathivanan, John Cappiello -1

机译：催化不对称合成中的C2-对称手性双（恶唑啉）-金属配合物
7. Development of Chiral Pincer Palladium Complexes Bearing a Pyrroloimidazolone Unit. Catalytic Use for Asymmetric Michael Addition [O] . -1

机译：含有吡咯的手性钳钯复合物的研制吡咯咪唑酮单元。不对称迈克尔的催化用途

Catalytic asymmetric electrophilic alpha-amination of alpha-cyanoketones in the presence of chiral palladium complexes

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