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Enantioselective synthesis of chiral 4H-pyran derivatives through [3+3] tandem reaction over a squaramide catalyst 方酰胺催化[3+3]串联反应手性4h -吡喃衍生物的对映选择性合成
Tetrahedron, asymmetry Pub Date : 2017-12-15 DOI: 10.1016/j.tetasy.2017.10.011
Zhonghe Wang, Yali Zhu, Jing Zhang, Jiawei Li, Min Wu, Xilong Yan, Yang Li, Ligong Chen
{"title":"Enantioselective synthesis of chiral 4H-pyran derivatives through [3+3] tandem reaction over a squaramide catalyst","authors":"Zhonghe Wang,&nbsp;Yali Zhu,&nbsp;Jing Zhang,&nbsp;Jiawei Li,&nbsp;Min Wu,&nbsp;Xilong Yan,&nbsp;Yang Li,&nbsp;Ligong Chen","doi":"10.1016/j.tetasy.2017.10.011","DOIUrl":"10.1016/j.tetasy.2017.10.011","url":null,"abstract":"<div><p>An efficient [3+3] tandem reaction<span> between 1-phenyl-3-methyl-5-pyrazolones and 2-(1-alkynyl)-2-alken-1-ones over a tertiary amine–squaramide catalyst is described. The pyran<span> fused pyrazolone derivatives were successfully obtained in 53–88% yields and with 62–84% ee by this synthetic methodology. This methodology involves easily accessible starting material, mild condition, satisfied yields and ee values. Additionally, when enynes were used as the substrates for the [3+3] cascade reaction, isomerized target products could be obtained directly.</span></span></p></div>","PeriodicalId":22237,"journal":{"name":"Tetrahedron, asymmetry","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2017-12-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/j.tetasy.2017.10.011","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"72452024","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 4
Synthesis of polyhydroxylated bicyclic tetrahydrofurans and tetrahydropyrans via a stereoselective domino cyclization/reduction reaction 立体选择性多米诺环化/还原反应合成多羟基化双环四氢呋喃和四氢吡喃
Tetrahedron, asymmetry Pub Date : 2017-12-15 DOI: 10.1016/j.tetasy.2017.10.001
Michał Malik, Piotr Cmoch, Mykhaylo A. Potopnyk, Sławomir Jarosz
{"title":"Synthesis of polyhydroxylated bicyclic tetrahydrofurans and tetrahydropyrans via a stereoselective domino cyclization/reduction reaction","authors":"Michał Malik,&nbsp;Piotr Cmoch,&nbsp;Mykhaylo A. Potopnyk,&nbsp;Sławomir Jarosz","doi":"10.1016/j.tetasy.2017.10.001","DOIUrl":"10.1016/j.tetasy.2017.10.001","url":null,"abstract":"<div><p><span><span>A novel reaction cascade involving a Lewis acid-induced migration of an isopropylidene protecting group followed by the formation of a </span>pyranose<span><span><span><span> or furanose ring and subsequent reduction of the hemiacetal is described. Depending on the reaction conditions, as well as, the </span>stereochemistry of the substrate, polyhydroxylated </span>tetrahydrofurans or </span>tetrahydropyrans<span> can be obtained in reasonable yields. The synthons used in this transformation were prepared via a highly stereoselective one-pot tandem reaction, consisting of a 1,4-Michael addition of vinylmagnesium bromide to </span></span></span><span>d</span><span>-glucose-derived cyclohexenone<span> followed by aldol reaction with 2,3-</span></span><em>O</em>-isopropylidene-<span>d</span>-glyceraldehyde.</p></div>","PeriodicalId":22237,"journal":{"name":"Tetrahedron, asymmetry","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2017-12-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/j.tetasy.2017.10.001","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"85448934","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 1
Stereoselective sulfoxidation catalyzed by achiral Schiff base complexes in the presence of serum albumin in aqueous media 在水介质中血清白蛋白存在下，非手性席夫碱络合物催化立体选择性亚砜化反应
Tetrahedron, asymmetry Pub Date : 2017-12-15 DOI: 10.1016/j.tetasy.2017.10.021
Jie Tang , Pengfei Yao , Fuping Huang , Meiyi Luo , Yi Wei , Hedong Bian
{"title":"Stereoselective sulfoxidation catalyzed by achiral Schiff base complexes in the presence of serum albumin in aqueous media","authors":"Jie Tang ,&nbsp;Pengfei Yao ,&nbsp;Fuping Huang ,&nbsp;Meiyi Luo ,&nbsp;Yi Wei ,&nbsp;Hedong Bian","doi":"10.1016/j.tetasy.2017.10.021","DOIUrl":"https://doi.org/10.1016/j.tetasy.2017.10.021","url":null,"abstract":"<div><p>Four coordination complexes <strong>ML</strong> derived from an achiral Schiff base ligand (H<sub>2</sub>L = 2,2′-[(1,2-ethanediyl)bis(nitrilopropylidyne)]bisphenol) have been synthesized and characterized. A method is described for the enantioselective oxidation of a series of aryl alkyl sulfides using the coordination complexes in the presence of serum albumins (SAs) in an aqueous medium at ambient temperature. The mixture of metal complexes with serum albumins is useful for inducing asymmetric catalysis. The complex, albumin source and substrate influence stereoselective sulfoxidation. At optimal pH with the appropriate oxidant, some of <strong>ML</strong>/SA systems are identified as very efficient catalysts, giving the corresponding sulfoxides in excellent chemical yield (up to 100%) and good enantioselectivity (up to 94% <em>ee</em>) in certain cases. UV–visible spectroscopic data provide evidence that stronger binding between the complex and serum albumin lead to higher enantioselectivity.</p></div>","PeriodicalId":22237,"journal":{"name":"Tetrahedron, asymmetry","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2017-12-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/j.tetasy.2017.10.021","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"91631054","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 8
A convergent approach towards the synthesis of the 2-alkyl-substituted tetrahydroquinoline alkaloid (−)-cuspareine 合成2-烷基取代四氢喹啉生物碱(−)库柏碱的收敛方法
Tetrahedron, asymmetry Pub Date : 2017-12-15 DOI: 10.1016/j.tetasy.2017.10.023
M.V. Madhubabu , R. Shankar , T. Krishna , Y. Satish Kumar , Y. Chiranjeevi , Ch. Muralikrishna , H. Rama Mohan , Satish S. More , M.V. Basaveswara Rao , Raghunadh Akula
{"title":"A convergent approach towards the synthesis of the 2-alkyl-substituted tetrahydroquinoline alkaloid (−)-cuspareine","authors":"M.V. Madhubabu ,&nbsp;R. Shankar ,&nbsp;T. Krishna ,&nbsp;Y. Satish Kumar ,&nbsp;Y. Chiranjeevi ,&nbsp;Ch. Muralikrishna ,&nbsp;H. Rama Mohan ,&nbsp;Satish S. More ,&nbsp;M.V. Basaveswara Rao ,&nbsp;Raghunadh Akula","doi":"10.1016/j.tetasy.2017.10.023","DOIUrl":"https://doi.org/10.1016/j.tetasy.2017.10.023","url":null,"abstract":"<div><p>A convergent approach towards the synthesis of the 2-alkyl-substituted tetrahydroquinoline alkaloid (−)-cuspareine via enantiospecific construction of the (<em>R</em>)-benzyl 2-formyl-3,4-dihydroquinoline-1(2<em>H</em>)-carboxylate. We have achieved an efficient enantiospecific synthesis of (−)-cuspareine starting from known key starting materials. The reactions employed for individual transformations are simple and high yielding, and the strategy could potentially be easily extended.</p></div>","PeriodicalId":22237,"journal":{"name":"Tetrahedron, asymmetry","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2017-12-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/j.tetasy.2017.10.023","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"91631059","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 2
Synthesis of chiral carbosilane dendrimers with l-cysteine and N-acetyl-l-cysteine on their surface and their application as chiral selectors for enantiomer separation by capillary electrophoresis 表面含l-半胱氨酸和n -乙酰-l-半胱氨酸的手性碳硅烷树状大分子的合成及其在毛细管电泳对映体分离中的应用
Tetrahedron, asymmetry Pub Date : 2017-12-15 DOI: 10.1016/j.tetasy.2017.10.028
Sara Quintana , María Ángeles García , María Luisa Marina , Rafael Gómez , F. Javier de la Mata , Paula Ortega
{"title":"Synthesis of chiral carbosilane dendrimers with l-cysteine and N-acetyl-l-cysteine on their surface and their application as chiral selectors for enantiomer separation by capillary electrophoresis","authors":"Sara Quintana ,&nbsp;María Ángeles García ,&nbsp;María Luisa Marina ,&nbsp;Rafael Gómez ,&nbsp;F. Javier de la Mata ,&nbsp;Paula Ortega","doi":"10.1016/j.tetasy.2017.10.028","DOIUrl":"https://doi.org/10.1016/j.tetasy.2017.10.028","url":null,"abstract":"<div><p><span>The synthesis of chiral carbosilane dendrimers functionalized with cysteine and </span><em>N</em><span>-acetylcysteine groups is presented. These dendrimers were obtained through thiol–ene addition reactions and their application as chiral selectors in capillary electrophoresis was investigated. Four drugs used as model compounds were analyzed under different experimental conditions observing that the use of a first generation dendrimer containing 4 terminal </span><em>N</em>-acetyl-<span>l</span><span><span><span>-cysteine groups enabled the enantiomeric discrimination of </span>razoxane with a discrimination power similar to that obtained with other powerful chiral selectors such as </span>cyclodextrins.</span></p></div>","PeriodicalId":22237,"journal":{"name":"Tetrahedron, asymmetry","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2017-12-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/j.tetasy.2017.10.028","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"91631062","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 11
The conjugate addition of enantiomerically pure lithium amides as chiral ammonia equivalents part III: 2012–2017 对映体纯锂酰胺作为手性氨等价物的共轭加成，第3部分:2012-2017
Tetrahedron, asymmetry Pub Date : 2017-12-15 DOI: 10.1016/j.tetasy.2017.10.031
Stephen G. Davies, Ai M. Fletcher, Paul M. Roberts, James E. Thomson
{"title":"The conjugate addition of enantiomerically pure lithium amides as chiral ammonia equivalents part III: 2012–2017","authors":"Stephen G. Davies,&nbsp;Ai M. Fletcher,&nbsp;Paul M. Roberts,&nbsp;James E. Thomson","doi":"10.1016/j.tetasy.2017.10.031","DOIUrl":"https://doi.org/10.1016/j.tetasy.2017.10.031","url":null,"abstract":"<div><p>This review covers further applications of the conjugate addition of enantiomerically pure lithium amides as chiral ammonia equivalents in asymmetric synthesis and provides an update since our last review of this area, which was published in 2012.</p></div>","PeriodicalId":22237,"journal":{"name":"Tetrahedron, asymmetry","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2017-12-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/j.tetasy.2017.10.031","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"136549435","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Stereochemistry abstracts 立体化学文摘
Tetrahedron, asymmetry Pub Date : 2017-12-15 DOI: 10.1016/S0957-4166(17)30538-4
{"title":"Stereochemistry abstracts","authors":"","doi":"10.1016/S0957-4166(17)30538-4","DOIUrl":"https://doi.org/10.1016/S0957-4166(17)30538-4","url":null,"abstract":"","PeriodicalId":22237,"journal":{"name":"Tetrahedron, asymmetry","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2017-12-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/S0957-4166(17)30538-4","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"136549436","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Stereoselection in the Betti reaction of valine methyl esters 缬氨酸甲酯Betti反应中的立体选择
Tetrahedron, asymmetry Pub Date : 2017-12-15 DOI: 10.1016/J.TETASY.2017.10.026
M. Capozzi, C. Cardellicchio
{"title":"Stereoselection in the Betti reaction of valine methyl esters","authors":"M. Capozzi, C. Cardellicchio","doi":"10.1016/J.TETASY.2017.10.026","DOIUrl":"https://doi.org/10.1016/J.TETASY.2017.10.026","url":null,"abstract":"","PeriodicalId":22237,"journal":{"name":"Tetrahedron, asymmetry","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2017-12-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"86191455","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 12
Amidation of carboxylic acids via the mixed carbonic carboxylic anhydrides and its application to synthesis of antidepressant (1S,2R)-tranylcypromine 混合碳羧酸酰胺化羧酸及其在抗抑郁药(1S,2R)-丙氨酰环丙氨酸合成中的应用
Tetrahedron, asymmetry Pub Date : 2017-12-15 DOI: 10.1016/j.tetasy.2017.10.015
Tetsuya Ezawa, Yuya Kawashima, Takuya Noguchi, Seunghee Jung, Nobuyuki Imai
{"title":"Amidation of carboxylic acids via the mixed carbonic carboxylic anhydrides and its application to synthesis of antidepressant (1S,2R)-tranylcypromine","authors":"Tetsuya Ezawa,&nbsp;Yuya Kawashima,&nbsp;Takuya Noguchi,&nbsp;Seunghee Jung,&nbsp;Nobuyuki Imai","doi":"10.1016/j.tetasy.2017.10.015","DOIUrl":"https://doi.org/10.1016/j.tetasy.2017.10.015","url":null,"abstract":"<div><p><span>Primary amidations of carboxylic acids </span><strong>1</strong> or <strong>3</strong> with NH<sub>4</sub>Cl in the presence of ClCO<sub>2</sub>Et and Et<sub>3</sub><span><span>N were developed to afford the corresponding primary amides in 22% to </span>quantitative yields<span>. Additionally, we have applied the amidation to the preparation of various amides containing hydroxamic acids and achieved the synthesis of (1</span></span><em>S</em>,2<em>R</em><span>)-tranylcypromine as an antidepressant medicine via Lossen rearrangement.</span></p></div>","PeriodicalId":22237,"journal":{"name":"Tetrahedron, asymmetry","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2017-12-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/j.tetasy.2017.10.015","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"90001170","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 9
Lipase-catalyzed kinetic resolution approach toward enantiomerically enriched 1-(β-hydroxypropyl)indoles 脂肪酶催化对映体富集1-(β-羟丙基)吲哚的动力学分解方法
Tetrahedron, asymmetry Pub Date : 2017-12-15 DOI: 10.1016/J.TETASY.2017.10.010
P. Borowiecki, I. Justyniak, Z. Ochal
{"title":"Lipase-catalyzed kinetic resolution approach toward enantiomerically enriched 1-(β-hydroxypropyl)indoles","authors":"P. Borowiecki, I. Justyniak, Z. Ochal","doi":"10.1016/J.TETASY.2017.10.010","DOIUrl":"https://doi.org/10.1016/J.TETASY.2017.10.010","url":null,"abstract":"","PeriodicalId":22237,"journal":{"name":"Tetrahedron, asymmetry","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2017-12-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"73802164","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 15
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