Asymmetric Addition of Oragnozinc Reagentsto Nitrones Enantiomeric Enhancement by A RacemicProduct-like Additive

机译：像RacemicProduct一样的添加剂将Oragnozinc试剂不对称地添加到硝基对映体中

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1.Introduction The development of efficient carbon-carbon bond formation by asymmetric nucleophilic addition to carbon-nitrogen double bond is quite important.Among the imine compounds,nitrone might be a promising candidate as the substrate because it possesses an electronegative oxygen,which can not only activate the carbon-nitrogen double bond but also coordinate to metals. The asymmetric addition of acetylide to nitrones is a useful method for the production of chiral propargylamines,which are versatile building blocks for preparation of the optically active nitrogen containing compounds and can also encounter as part of biologically active compounds.Although several diastereoselective methods for nucleophilic addition of zinc acetylides to nitrones were recently reported, the enatioselective methods were limited and are still regarded as one of the challenging problems especially in terms of availability of chiral auxiliaries.

机译：1引言通过碳氮双键的不对称亲核加成反应形成有效的碳碳键非常重要。在亚胺化合物中，亚硝基可能是有前途的候选物，因为它具有负电性氧，不能不仅激活碳氮双键，而且还与金属配位。乙炔基不对称地添加乙炔化物是生产手性炔丙基胺的有用方法，手性炔丙基胺是制备光学活性含氮化合物的通用结构单元，也可以作为生物活性化合物的一部分。尽管有几种非对映选择性的亲核加成方法最近报道了将乙酰锌锌转化为硝酮，对映选择性方法受到限制，仍然被认为是具有挑战性的问题之一，特别是在手性助剂的可获得性方面。

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来源
《18th International Symposium on Fine Chemistry and Functional Polymers,4th IUPAC International Symposium on Novel Materials and Their Synthesis(第18届国际精细化学和功能高分子学术讨论会暨第四届IUPAC 国际新型材料及其制备学术讨论会）》|2008年|39-41|共3页
会议地点 Zhenjiang(CN);Zhenjiang(CN);Zhenjiang(CN);Zhenjiang(CN)
作者
Weilin Wei; Atsuko Konishi; Yoshihira Hamamoto; Masato Kobayashi; Yutaka Ukaji; Katsuhiko Inomata;
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作者单位

Division of Material Sciences,Graduate School of Natural Science and Technology,Kanazawa University,Kakuma,Kanazawa,920-1192 Japan;

Division of Material Sciences,Graduate School of Natural Science and Technology,Kanazawa University,Kakuma,Kanazawa,920-1192 Japan;

Division of Material Sciences,Graduate School of Natural Science and Technology,Kanazawa University,Kakuma,Kanazawa,920-1192 Japan;

Division of Material Sciences,Graduate School of Natural Science and Technology,Kanazawa University,Kakuma,Kanazawa,920-1192 Japan;

Division of Material Sciences,Graduate School of Natural Science and Technology,Kanazawa University,Kakuma,Kanazawa,920-1192 Japan;

Division of Material Sciences,Graduate School of Natural Science and Technology,Kanazawa University,Kakuma,Kanazawa,920-1192 Japan;

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原文格式 PDF
正文语种 eng
中图分类
关键词
asymmetric nucleophilic addition; tartaric acid esters; nitrone; hydroxylamine; enantiomeric enhancement;

机译：不对称亲核加成;酒石酸酯;亚硝基;羟胺;对映体增强;

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专利

1. Asymmetric addition of phenylzinc reagents to C-alkynyl nitrones. Enantiomeric enhancement by a product-like additive [J] . Wei W, Hamainoto Y, Ukaji Y, Tetrahedron, Asymmetry: The International Journal for Repid Publication on all Aspects of Asymmetry in Orgainc, Inorganic, Organometallic, Physical and Bio-Organic Chemistry . 2008,第4期

机译：苯基锌试剂不对称加成到C-炔基硝酮上。通过类似产品的添加剂增强对映体
2. Nucleophilic addition of nitrones to ketones: development of a new catalytic asymmetric nitrone-aldol reaction [J] . Anders Bogevig, Kurt V.Gothelf, Karl Anker Jorgensen Chemistry: A European journal . 2002,第24期

机译：酮类化合物的硝基亲核加成反应：新催化不对称硝酮-醛醇缩合反应的发展
3. The use of enantiomerically pure ketene dithioacetal bis(sulfoxides) in highly diastereoselective intramolecular nitrone cycloadditions. Application in the total synthesis of the β-amino acid (-)-cispentacin and the first asymmetric synthesis of cis-(3R [J] . Varinder K. Aggarwal, Stephen Roseblade, Rikki Alexander Organic & biomolecular chemistry . 2003,第4期

机译：对映体纯的乙烯酮二硫缩醛双（亚砜）在高度非对映选择性分子内硝酮环加成反应中的使用。在β-氨基酸（-）-顺喷菌素的全合成和顺式-（3R）的首次不对称合成中的应用
4. Asymmetric Addition of Oragnozinc Reagentsto Nitrones Enantiomeric Enhancement by A RacemicProduct-like Additive [C] . International symposium on fine chemistry and functional polymers . 2008

机译：通过脱液产品样添加剂的非对称添加Oragnozinc Regentsto硝基对映体增强
5. The design and synthesis of novel chiral Z-nitrones with applications towards the syntheses of enantiomerically pure 4-hydroxy amino acids. [D] . Stanko, John August. 2009

机译：新型手性Z-硝酮的设计和合成及其对映体纯的4-羟基氨基酸的合成应用。
6. Asymmetric Catalysis Special Feature Part II: Cu(I)-catalyzed direct addition and asymmetric addition of terminal alkynes to imines [O] . Chunmei Wei, Joel T. Mague, Chao-Jun Li 2004

机译：不对称催化特征第二部分：末端炔烃在亚胺上的铜（I）催化直接加成和不对称加成
7. Asymmetric addition of phenylzinc reagents to C-alkynyl nitrones. Enantiomeric enhancement by a product-like additive [O] . Wei, Weilin, Hamamoto, Yoshihira, Ukaji, Yutaka, 2008

机译：苯基锌试剂与C-炔基硝酮的不对称加成。产品类添加剂的对映体增强作用

Asymmetric Addition of Oragnozinc Reagentsto Nitrones Enantiomeric Enhancement by A RacemicProduct-like Additive

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