Simple preparation of enantiomeric Michael adducts of thiophenol to chalcones: easily available new chiral building blocks

Skarzewski J.; Turowska-Tyrk I.; Zielinska-Blajet M.

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Simple preparation of enantiomeric Michael adducts of thiophenol to chalcones: easily available new chiral building blocks

机译：硫酚与对苯二酚的对映体迈克尔加合物的简单制备方法：易于获得的新型手性结构单元

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A facile and enantioselective method for the multigram preparation of the title compounds is described. The Michael addition of thiophenols to chalcones catalyzed by (+)-cinchonine, followed by crystallization, led to the corresponding adducts 2 in up to > 95% e.e. The stereoselective Beckmann rearrangement of the oxime of (+)-1,3-diphenyl-3-phenylsulfanylpropan-1-one 2a gives the anilide of (R)-(+)-3-phenyl-3-phenylsulfanylpropanoic acid (as determined by X-ray analysis) and alcoholysis leads to the corresponding enantiomerically pure ethyl ester. (C) 2001 Elsevier Science Ltd. All rights reserved. [References: 28]

机译：描述了一种用于标题化合物的多谱图制备的简便和对映选择性的方法。由（+）-辛可宁催化将硫代酚迈克尔加到查耳酮中，随后结晶，导致相应的加合物2的含量高达> 95％e.e.。（+）-1,3-二苯基-3-苯基硫烷基丙烷-1-酮2a肟的立体选择性贝克曼重排得到（R）-（+）-3-苯基-3-苯基硫烷基丙酸的苯胺（通过X射线分析）和醇解反应生成相应的对映体纯的乙基酯。（C）2001 Elsevier ScienceLtd。保留所有权利。 [参考：28]

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《Tetrahedron, Asymmetry: The International Journal for Repid Publication on all Aspects of Asymmetry in Orgainc, Inorganic, Organometallic, Physical and Bio-Organic Chemistry》 |2001年第13期|共6页
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Skarzewski J.; Turowska-Tyrk I.; Zielinska-Blajet M.;
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1. Simple preparation of enantiomeric Michael adducts of thiophenol to chalcones: easily available new chiral building blocks [J] . Skarzewski J., Turowska-Tyrk I., Zielinska-Blajet M. Tetrahedron, Asymmetry: The International Journal for Repid Publication on all Aspects of Asymmetry in Orgainc, Inorganic, Organometallic, Physical and Bio-Organic Chemistry . 2001,第13期

机译：硫酚与对苯二酚的对映体迈克尔加合物的简单制备方法：易于获得的新型手性结构单元
2. Chiral 2,4,6-trihydroxycyclohexanones as potent building blocks: A convenient method for the preparation of enantiomerically pure acyclic 1,3-diols [J] . Kirsch SF, Bach T Synthesis: International Journal of Methods in Synthetic Organic Chemistry . 2005,第16期

机译：手性2,4,6-三羟基环己酮作为有效的构建基块：制备对映体纯的无环1,3-二醇的便捷方法
3. A novel route to a chiral building block for the preparation of cyclopentenyl carbocyclic nucleosides. Synthesis and anticancer activity of enantiomeric neplanocins A [J] . Lukasik Beata, Mikina Maciej, Mikolajczyk Marian, RSC Advances . 2020,第53期

机译：用于制备环戊烯基核苷的手性积木的新途径。对映体Neplanocins A的合成和抗癌活性
4. BIO-BASED THERMOSETS PREPARED USING MICHAEL ADDITION OF FURAN AND ISOSORBIDE BUILDING BLOCKS [C] . Xi Chu, John J.La Scala, Giuseppe R. Palmese SAMPE Conference;Society for the Advancement of Material and Process Engineering . 2019

机译：使用迈克尔添加的呋喃和异硫醚砌块制备基于生物的热敏剂
5. Iridium catalyzed aromatic borylation and its applications in one-pot preparations of substituted aromatic building blocks. [D] . Chotana, Ghayoor Abbas. 2009

机译：铱催化的芳香族硼酸酯化及其在一锅法制备取代的芳香族结构单元中的应用。
6. New eco-friendly animal bone meal catalysts for preparation of chalcones and aza-Michael adducts [O] . Yassine Riadi, Younes Abrouki, Rachid Mamouni, 2012

机译：用于制备查耳酮和氮杂-迈克尔加合物的新型环保动物骨粉催化剂
7. A novel route to a chiral building block for the preparation of cyclopentenyl carbocyclic nucleosides. Synthesis and anticancer activity of enantiomeric neplanocins A [O] . Beata Łukasik, Maciej Mikina, Marian Mikołajczyk, 2020

机译：用于制备环戊烯基核苷的手性积木的新途径。对映体Neplanocins A的合成和抗癌活性

Simple preparation of enantiomeric Michael adducts of thiophenol to chalcones: easily available new chiral building blocks

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