Stereodivergent Aminocatalytic Synthesis of Z- and E-Trisubstituted Double Bonds from Alkynals

Marzo Leyre; Luis-Barrera Javier; Mas-Balleste Ruben; Garcia Ruano Jose Luis; Aleman Jose

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Stereodivergent Aminocatalytic Synthesis of Z- and E-Trisubstituted Double Bonds from Alkynals

机译：炔烃的Z-和E-三取代双键的立体发散氨基催化合成

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A highly diastereoselective synthesis of trisubstituted Z- or E-enals, which are important intermediates in organic synthesis, as well as being present in natural products, is described using different alkynals and nucleophiles as starting materials. Diastereocontrol is mainly governed by the appropriate catalyst. Therefore, those reactions controlled by steric effects, such as the JOrgensen-Hayashi's catalyst, give access to E isomers, and those catalysts that facilitate hydrogen bonding, such as tetrazol-pyrrolidine Ley's catalyst, allow the synthesis of Z isomers. A stereochemical model based on DFT calculations is proposed.

机译：描述了使用不同的炔基和亲核试剂作为起始原料的三取代的Z-或E-烯醛的高度非对映选择性合成，这是有机合成中的重要中间体，也存在于天然产物中。非对映控制主要由适当的催化剂控制。因此，受空间效应控制的那些反应（例如约根森-哈耶希（Jorgensen-Hayashi）催化剂）可接触E异构体，而那些促进氢键结合的催化剂（例如四唑-吡咯烷Ley's催化剂）可合成Z异构体。提出了一种基于DFT计算的立体化学模型。

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《Chemistry: A European journal》 |2016年第46期|共11页
作者
Marzo Leyre; Luis-Barrera Javier; Mas-Balleste Ruben; Garcia Ruano Jose Luis; Aleman Jose;
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正文语种 eng
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关键词
alkynals; aminocatalysis; double bonds; enals; protonation;

机译：炔;氨基催化;双键;烯;质子化;

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1. Stereodivergent Aminocatalytic Synthesis of Z- and E-Trisubstituted Double Bonds from Alkynals [J] . Marzo Leyre, Luis-Barrera Javier, Mas-Balleste Ruben, Chemistry: A European journal . 2016,第46期

机译：炔烃的Z-和E-三取代双键的立体发散氨基催化合成
2. Ligand-Controlled Cobalt-Catalyzed Transfer Hydrogenation of Alkynes: Stereodivergent Synthesis of Z- and E-Alkenes [J] . Shaomin Fu, Nan-Yu Chen, Xufang Liu, Journal of the American Chemical Society . 2016,第27期

机译：炔烃的配体控制的钴催化转移氢化：Z和E烯烃的立体发散合成
3. An efficient stereoselective synthesis of Z-(2S)- and Z-(2R)-2-tert-butoxycarbonylamino-6-hydroxyhex-4-enoic acid, key intermediates in the synthesis of (2S, 4S, 5R)-(-)- and (2R,4R,5S)-(+)-bulgecinine [J] . Karen E.Holt, Jonathan P.Swift, Mark E.B.Smith, Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry . 2002,第8期

机译：Z-（2S）-和Z-（2R）-2-叔丁氧基羰基氨基-6-羟基己基-4-烯酸的高效立体选择性合成，这是合成（2S，4S，5R）-（-）的关键中间体-和（2R，4R，5S）-（+）-bulgecinine
4. A Double Frequency Ripple Suppression Control in Quasi Z- Source Inverter [C] . S. Priyanka, F. X. Edwin Deepak 2018 National Power Engineering Conference . 2018

机译：准Z源逆变器的双频纹波抑制控制
5. Stereodivergent Synthesis of Enantioenriched Five- and Six-Membered Cyclic-1,3-diols and Applications Toward Library Synthesis. [D] . Singh, Gurpreet. 2015

机译：富含对映体的五元和六元环-1,3-二醇的立体发散合成及其在文库合成中的应用。
6. Stereospecific Formation of E- and Z- Disubstituted Double Bonds by Dehydratase Domains from Modules 1 and 2 of the Fostriecin Polyketide Synthase [O] . Dhara D. Shah, Young-Ok You, David E. Cane -1

机译：E-和Z-双取代双键的立体定向形成由脱水酶域的Fostriecin聚酮化合物合酶的模块1和2。
7. 1, 1, 2, 2-Tetramethyl-1, 2-bis(phenylthiomethyl)disilane, a Flexible Ligand for the Construction of Macrocyclic, Mesocyclic, and Bridged Dithioether Complexes. Synthesis of the Bis-silylated Olefins Z-(PhSCH2)Me2SiC(H)dC(Ar)SiMe2(CH2SPh) by Catalytic Activation of the Si-Si Bond [O] . -1

机译：1,1,2,2-四甲基-1,2-双（苯硫代甲基）硅烷，柔性配体，用于构建大环，间环和桥接二氧醚络合物。通过Si-Si键的催化活化合成双叶片烯烃Z-（PHSCH2）Me2SIC（H）DC（AR）SIME2（CH2SPH）的合成

Stereodivergent Aminocatalytic Synthesis of Z- and E-Trisubstituted Double Bonds from Alkynals

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