{"title":"Applications of Danishefsky’s dienes in asymmetric Oxo-Diels-Alder reactions","authors":"Afsaneh Taheri kal Koshvandi, Majid M. Heravi","doi":"10.1016/j.tetasy.2017.10.030","DOIUrl":"10.1016/j.tetasy.2017.10.030","url":null,"abstract":"<div><p><span><span>Applications of Danishefsky’s dienes in catalytic asymmetric hetero-Diels-Alder (AHDA) reactions or specifically, their asymmetric Oxo-Diels-Alder (AOxo-DA) reactions with appropriate dienophiles are highlighted in detail, including the preparation of catalysts with discussion from a mechanistic points of view. Danishefsky’s dienes are effective and useful compounds for the synthesis of optically active six-membered rings such as dihydropyrones, dihydropyridones and dihydropyrans. Due to the broad range of the overall subject, we have limited ourselves, to the recent developments in the utility of Danishefsky’s dienes in the reaction with </span>carbonyl compounds (aldehydes, </span>ketones and 1,2-dicarbonyl compounds) in asymmetric Oxo-Diels-Alder (AOxo-DA) reactions.</p></div>","PeriodicalId":22237,"journal":{"name":"Tetrahedron, asymmetry","volume":"28 11","pages":"Pages 1506-1556"},"PeriodicalIF":0.0,"publicationDate":"2017-11-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/j.tetasy.2017.10.030","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"78520326","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}
Kamal Usef Sadek , Ramadan Ahmed H. Mekheimer , Mohamed Abd-Elmonem , Afaf Abdel-Hameed , Mohamed Hilmy Elnagdi
{"title":"Recent developments in the enantioselective synthesis of polyfunctionalized pyran and chromene derivatives","authors":"Kamal Usef Sadek , Ramadan Ahmed H. Mekheimer , Mohamed Abd-Elmonem , Afaf Abdel-Hameed , Mohamed Hilmy Elnagdi","doi":"10.1016/j.tetasy.2017.10.020","DOIUrl":"10.1016/j.tetasy.2017.10.020","url":null,"abstract":"<div><p><span>Recent developments in the synthesis of 4H- and 2H-pyrans as well as structurally related chromene derivatives that have enabled the enantioselective synthesis of these scaffolds have been surveyed. The role of chiral catalysts in orienting initial reactions of active methylenes, methines and </span>methyl ketones<span><span>, to unsaturated ketones<span> and nitriles in multi-component reactions or Friedel–Craft alkylations of phenols is discussed to show their involvement in transition states leading to end products. Chromene synthesis via [4+2] cycloadditions, [3+3] and [4+2] annulations as well as ring opening and </span></span>recyclization<span> leading to high enantio- and diasteroselectivity is also demonstrated. The enantioselectivity in such catalytic asymmetric reactions despite starting with non-chiral starting materials is discussed. On the other hand, in surveying ring opening and recyclization, the starting materials are chiral and the chiral center was not part of the reaction leading to the final product.</span></span></p></div>","PeriodicalId":22237,"journal":{"name":"Tetrahedron, asymmetry","volume":"28 11","pages":"Pages 1462-1485"},"PeriodicalIF":0.0,"publicationDate":"2017-11-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/j.tetasy.2017.10.020","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"86291472","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}
{"title":"Immobilization of Lecitase® ultra on recyclable polymer support: application in resolution of trans-methyl (4-methoxyphenyl)glycidate in organic solvents","authors":"Thenkrishnan Kumaraguru, Tirunagari Harini, Shalini Basetty","doi":"10.1016/j.tetasy.2017.10.006","DOIUrl":"10.1016/j.tetasy.2017.10.006","url":null,"abstract":"<div><p><span><span>Lecitase® Ultra was immobilized on epoxy-activated polymer (DILBEAD-VWR) functionalized with polyethyleneimine via adsorption and crosslinking with </span>glutaraldehyde. The resolution of methyl </span><em>trans</em>-(±)-3-(4-methoxyphenyl) glycidate was carried out in xylene (<em>e.e.</em><span> >99%, conversion 50%). The enzyme is not inhibited by the 4-methoxy phenyl acetaldehyde produced during hydrolysis and the immobilized enzyme with 7% moisture content works efficiently in an organic phase. While the immobilized enzyme can be recycled several times, the polymer support can also be recycled after removing the immobilized enzyme by washing with 1 M HCl.</span></p></div>","PeriodicalId":22237,"journal":{"name":"Tetrahedron, asymmetry","volume":"28 11","pages":"Pages 1612-1617"},"PeriodicalIF":0.0,"publicationDate":"2017-11-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/j.tetasy.2017.10.006","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"75590810","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}
{"title":"An asymmetric synthesis of (+)-monomorine I","authors":"Masaki Asai , Yukiko Takemoto , Ayaka Deguchi , Yasunao Hattori , Hidefumi Makabe","doi":"10.1016/j.tetasy.2017.09.008","DOIUrl":"10.1016/j.tetasy.2017.09.008","url":null,"abstract":"<div><p><span>The synthesis of (+)-monomorine I, an indolizidine alkaloid isolated from </span><span><em>Monomorium pharaonis</em></span>, has been achieved. The 2,6-<em>cis</em><span>-piperidine ring moiety of (+)-monomorine I was constructed using diastereoselective aminopalladation. Chain elongation via cross-metathesis using Hoveyda-Grubbs 2nd catalyst followed by deprotection of the Cbz group and cyclic reductive hydroamination afforded (+)-monomorine I.</span></p></div>","PeriodicalId":22237,"journal":{"name":"Tetrahedron, asymmetry","volume":"28 11","pages":"Pages 1582-1586"},"PeriodicalIF":0.0,"publicationDate":"2017-11-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/j.tetasy.2017.09.008","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"72793002","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}
Zhi-Feng Sun , Lu-Nan Zhou , Yifei Meng , Tao Zhang , Zhen-Ting Du , Huaiji Zheng
{"title":"Concise asymmetric synthesis of the sex pheromone of the tea tussock moth","authors":"Zhi-Feng Sun , Lu-Nan Zhou , Yifei Meng , Tao Zhang , Zhen-Ting Du , Huaiji Zheng","doi":"10.1016/j.tetasy.2017.09.007","DOIUrl":"10.1016/j.tetasy.2017.09.007","url":null,"abstract":"<div><p><span><span>A concise asymmetric total synthesis of the sex pheromone of the tea </span>tussock moth has been achieved from commercially available starting materials. The chiral moiety was introduced by Evans’ template and the key C</span><img><span>C bond construction was accomplished through Julia-Kocienski coupling and Wittig olefination. The salient characteristic of our synthetic route is that it is protecting a group free.</span></p></div>","PeriodicalId":22237,"journal":{"name":"Tetrahedron, asymmetry","volume":"28 11","pages":"Pages 1562-1567"},"PeriodicalIF":0.0,"publicationDate":"2017-11-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/j.tetasy.2017.09.007","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"85098621","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}
Sripragna Burugupalli, Yupu Qiao, Allan D. Headley
{"title":"Highly enantioselective organocatalysis of the Michael addition of benzyloxyacetaldehyde to nitroolefins","authors":"Sripragna Burugupalli, Yupu Qiao, Allan D. Headley","doi":"10.1016/j.tetasy.2017.09.018","DOIUrl":"10.1016/j.tetasy.2017.09.018","url":null,"abstract":"<div><p>A novel category of di(<em>N</em>,<em>N</em><span>-dimethylbenzylamine)prolinol silyl ether<span><span> catalyst, which when used in conjunction with an acidic co-catalyst, generates an ammonium salt<span> supported organocatalyst<span><span>. This catalytic system is shown to be very effective for the Michael reaction of benzyloxyacetaldehyde and various nitroolefins in </span>isopropanol<span>. Excellent enantioselectivities (up to 99%) and </span></span></span></span>diastereoselectivities (</span></span><em>syn</em>/<em>anti</em> of 75:25) and short reaction times were obtained. The presence of the bulky OTMS group combined with the presence of two large <em>N</em>,<em>N</em><span>-dimethylbenzyl ammonium ion groups accounts for the effectiveness of this catalytic system.</span></p></div>","PeriodicalId":22237,"journal":{"name":"Tetrahedron, asymmetry","volume":"28 11","pages":"Pages 1608-1611"},"PeriodicalIF":0.0,"publicationDate":"2017-11-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/j.tetasy.2017.09.018","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"88243197","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}
Muhammad Faisal , Danish Shahzad , Aamer Saeed , Bhajan Lal , Shomaila Saeed , Fayaz Ali Larik , Pervaiz Ali Channar , Parvez Ali Mahesar , Jamaluddin Mahar
{"title":"Review on asymmetric synthetic methodologies for chiral isoquinuclidines; 2008 to date","authors":"Muhammad Faisal , Danish Shahzad , Aamer Saeed , Bhajan Lal , Shomaila Saeed , Fayaz Ali Larik , Pervaiz Ali Channar , Parvez Ali Mahesar , Jamaluddin Mahar","doi":"10.1016/j.tetasy.2017.10.013","DOIUrl":"10.1016/j.tetasy.2017.10.013","url":null,"abstract":"<div><p>Isoquinuclidines constitute the central structural nucleus of numerous biologically active natural products<span><span><span><span>, for example, iboga alkaloids such as </span>ibogamine<span> and catharanthine as well as non-indole-containing alkaloids such as the dioscorine and the cannivonines. Furthermore, in medicinal and pharmaceutical </span></span>chemistry, the isoquinuclidine core is commonly employed as a rigid azabicyclic scaffold, thus providing significant precursors in the synthesis of numerous valuable alkaloids. Summarizing well-organized approaches to access the chiral isoquinuclidine structural centerpiece signifies a significant endeavor not only for developing biologically active natural products but also enhancing biological researches that can lead to possible </span>drug discovery<span>. Over time, the values and methodologies for the asymmetric synthesis of chiral isoquinuclidines are increasing; hence to advance asymmetric synthesis, this review combines and discusses the pros and cons of each synthesis techniques from 2008. This review should be helpful for promoting further developments of asymmetric synthetic methodologies and for medicinal chemistry.</span></span></p></div>","PeriodicalId":22237,"journal":{"name":"Tetrahedron, asymmetry","volume":"28 11","pages":"Pages 1445-1461"},"PeriodicalIF":0.0,"publicationDate":"2017-11-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/j.tetasy.2017.10.013","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"73490549","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}
Iwona E. Głowacka, Dorota G. Piotrowska, Andrzej E. Wróblewski, Aleksandra Trocha
{"title":"Synthesis of the four enantiomers of diethyl 1,2-di(N-Boc-amino)propylphosphonates","authors":"Iwona E. Głowacka, Dorota G. Piotrowska, Andrzej E. Wróblewski, Aleksandra Trocha","doi":"10.1016/j.tetasy.2017.09.003","DOIUrl":"10.1016/j.tetasy.2017.09.003","url":null,"abstract":"<div><p><span>A simple and efficient synthetic strategy to all four enantiomerically pure diethyl 1,2-di(</span><em>N</em>-Boc-amino)propylphosphonates has been elaborated starting from the corresponding <em>N</em>-[(<em>R</em>)-(1-phenylethyl)]aziridine-(2<em>S</em>)- and <em>N</em>-[(<em>S</em>)-(1-phenylethyl)]aziridine-(2<em>R</em><span><span>)-carboxaldehydes, employing a one-pot three-components Kabachnik-Fields reaction followed by the hydrogenolytic removal of the chiral auxiliary and </span>aziridine ring opening with simultaneous protection of the amino groups as the </span><em>N</em>-Boc derivatives.</p></div>","PeriodicalId":22237,"journal":{"name":"Tetrahedron, asymmetry","volume":"28 11","pages":"Pages 1602-1607"},"PeriodicalIF":0.0,"publicationDate":"2017-11-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/j.tetasy.2017.09.003","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"82645850","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}
Konstantin N. Gavrilov , Sergey V. Zheglov , Ilya V. Chuchelkin , Marina G. Maksimova , Ilya D. Firsin , Andrew N. Fitch , Vladimir V. Chernyshev , Alexander V. Maximychev , Alexander M. Perepukhov
{"title":"Tartaric acid-derived chiral phosphite-type P,N-ligands: behavioural features in Pd-catalyzed asymmetric transformations","authors":"Konstantin N. Gavrilov , Sergey V. Zheglov , Ilya V. Chuchelkin , Marina G. Maksimova , Ilya D. Firsin , Andrew N. Fitch , Vladimir V. Chernyshev , Alexander V. Maximychev , Alexander M. Perepukhov","doi":"10.1016/j.tetasy.2017.09.011","DOIUrl":"10.1016/j.tetasy.2017.09.011","url":null,"abstract":"<div><p><span><span>A practical synthesis of new phosphoramidite, </span>phosphite and diamidophosphite </span><em>P</em>,<em>N</em>-ligands derived from (<em>R</em>,<em>R</em>)-tartaric acid was carried out. A study of these chiral inducers showed them to provide up to 93% <em>ee</em><span> in the Pd-catalyzed asymmetric allylations of (</span><em>E</em>)-1,3-diphenylallyl acetate, up to 84% <em>ee</em><span> in the Pd-catalyzed asymmetric alkylation<span><span> of cinnamyl acetate with </span>ethyl 2-oxocyclohexane-1-carboxylate and up to 63% </span></span><em>ee</em> in the Pd-catalyzed desymmetrization of <em>N</em>,<em>N</em>′-ditosyl-<em>meso</em><span>-cyclopent-4-ene-1,3-diol biscarbamate. The effects of the structural modules, such as the nature of the phosphorus-containing ring or exocyclic substituent as well as of the nature of palladium<span> source on the catalytic activity and enantioselectivity were investigated.</span></span></p></div>","PeriodicalId":22237,"journal":{"name":"Tetrahedron, asymmetry","volume":"28 11","pages":"Pages 1633-1643"},"PeriodicalIF":0.0,"publicationDate":"2017-11-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/j.tetasy.2017.09.011","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"73053939","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}