Jayaraman Kannappan , Aditya N. Khanvilkar , Gourav M. Upadhyay , Ashutosh V. Bedekar
{"title":"Benzyl isobornyl amines: a simple and practical class of NMR discriminating agents for effective chiral recognition of acids","authors":"Jayaraman Kannappan , Aditya N. Khanvilkar , Gourav M. Upadhyay , Ashutosh V. Bedekar","doi":"10.1016/j.tetasy.2017.08.007","DOIUrl":"10.1016/j.tetasy.2017.08.007","url":null,"abstract":"<div><p>The design and synthesis of a few simple <em>N</em>-benzyl derivatives of isobornyl amine is presented. The derivatives have been assessed as chiral solvating agents for effective discrimination of the signals of some acids in NMR analysis. The single crystal X-ray analysis of the salts of (<em>R</em>)-mandelic acid with two of the title derivatives help to understand the supramolecular interactions and assign the induced chemical shifts in <sup>1</sup><span>H NMR analysis. The title derivative is found to be suitable for quantitative determination of the enantiomeric<span> excess of unknown enantiomeric purity as well as being efficient in resolving racemic mandelic acid.</span></span></p></div>","PeriodicalId":22237,"journal":{"name":"Tetrahedron, asymmetry","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2017-10-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/j.tetasy.2017.08.007","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"72782324","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}
Ihssene Chabour , Luis M. Castelló , Juan Mancebo-Aracil , María Martín-Rodríguez , María de Gracia Retamosa , Carmen Nájera , José M. Sansano
{"title":"Dual chiral silver catalyst in the synthetic approach to the core of hepatitis C virus inhibitor GSK 625433 using enantioselective 1,3-dipolar cycloaddition of azomethine ylides and electrophilic alkenes","authors":"Ihssene Chabour , Luis M. Castelló , Juan Mancebo-Aracil , María Martín-Rodríguez , María de Gracia Retamosa , Carmen Nájera , José M. Sansano","doi":"10.1016/j.tetasy.2017.08.011","DOIUrl":"10.1016/j.tetasy.2017.08.011","url":null,"abstract":"<div><p>The asymmetric 1,3-dipolar cycloaddition of an imino ester <strong>5</strong> with <em>tert-</em><span>butyl acrylate<span> is catalyzed by a dual chiral silver(I) complex formed from a chiral phosphoramidite </span></span><strong>14</strong> and the chiral silver(I) binolphosphate (<em>R</em>)-<strong>17</strong><span>. This reaction is selected to achieve the synthesis of enantiomerically enriched key structures to access the third generation of GSK HCV inhibitors. The scope of this dual chiral catalytic system is analyzed by employing different imino esters and dipolarophiles, and also compared with the same cycloaddition reactions performed with the chiral phosphoramidite </span><strong>14</strong>·AgClO<sub>4</sub> complex.</p></div>","PeriodicalId":22237,"journal":{"name":"Tetrahedron, asymmetry","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2017-10-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/j.tetasy.2017.08.011","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"78626690","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}
Karolina Kamińska , Elżbieta Wojaczyńska , Claudio Santi , Luca Sancineto , Marianna Francesca Pensa , Andrzej Kochel , Robert Wieczorek , Jacek Wojaczyński , Gauthier Slupski
{"title":"An enantiopure diselenide based on a chiral bicyclic backbone—synthesis and configuration assignment","authors":"Karolina Kamińska , Elżbieta Wojaczyńska , Claudio Santi , Luca Sancineto , Marianna Francesca Pensa , Andrzej Kochel , Robert Wieczorek , Jacek Wojaczyński , Gauthier Slupski","doi":"10.1016/j.tetasy.2017.08.008","DOIUrl":"10.1016/j.tetasy.2017.08.008","url":null,"abstract":"<div><p><span><span>An enantiomerically pure </span>diselenide<span> containing two chiral bicyclic subunits was prepared from the respective halides<span>. The stereochemical outcome of the reaction was established via NMR spectroscopy and X-ray </span></span></span>diffraction measurements.</p></div>","PeriodicalId":22237,"journal":{"name":"Tetrahedron, asymmetry","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2017-10-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/j.tetasy.2017.08.008","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"85849669","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":"A closer look on various synthetic routes to Callystatin A: a cytotoxic marine sponge polyketide","authors":"Aamer Saeed, Babar Hussain Shah, Rabia Qamar","doi":"10.1016/j.tetasy.2017.08.015","DOIUrl":"10.1016/j.tetasy.2017.08.015","url":null,"abstract":"<div><p><span>Callystatin A<span><span>, a polyketide </span>marine natural product, has been known since 1997 after its isolation from the sponge </span></span><span><em>Callyspongia</em><em> truncata</em></span><span> by Kobayashi et al. It belongs to the leptomcyin family of natural products with a highly conjugated and stereodefined skeleton. The challenging structural topographies and remarkable anti-proliferative properties of (−)-Callystatin A stimulated many researchers to pursue the total synthesis of this marine polyketide. This review is exclusively focused on the research undertaken towards the concise, asymmetric total synthesis of Callystatin A over the last two decades. The various target oriented synthetic pathways are discussed in a chronological order to give a comprehensive overview.</span></p></div>","PeriodicalId":22237,"journal":{"name":"Tetrahedron, asymmetry","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2017-09-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/j.tetasy.2017.08.015","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"89218764","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}
Ingrid C.R. Costa , Rodrigo Octavio M.A. de Souza , Uwe T. Bornscheuer
{"title":"Asymmetric synthesis of serinol-monoesters catalyzed by amine transaminases","authors":"Ingrid C.R. Costa , Rodrigo Octavio M.A. de Souza , Uwe T. Bornscheuer","doi":"10.1016/j.tetasy.2017.08.012","DOIUrl":"10.1016/j.tetasy.2017.08.012","url":null,"abstract":"<div><p><span>The asymmetric synthesis<span> of serinol-derivatives was investigated employing different amine transaminases<span><span> as biocatalysts. Under the optimized conditions conversions up to 92% and excellent </span>enantiomeric excesses up to 99% ee were obtained providing access to both, the (</span></span></span><em>R</em>)- and (<em>S</em>)-configurations of the serinol-monoester (2-amino-3-hydroxypropyl hexanoate).</p></div>","PeriodicalId":22237,"journal":{"name":"Tetrahedron, asymmetry","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2017-09-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/j.tetasy.2017.08.012","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"73869078","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}
Matthew W.D. Perry, Anders Eriksson, Marie Rydén Landergren
{"title":"On the absolute configuration of 1-cyclopropylethan-1-amine","authors":"Matthew W.D. Perry, Anders Eriksson, Marie Rydén Landergren","doi":"10.1016/j.tetasy.2017.08.005","DOIUrl":"10.1016/j.tetasy.2017.08.005","url":null,"abstract":"<div><p><span><span>We observed a discrepancy between the reported specific rotation for the enantiomers of 1-cyclopropylethan-1-amine and the values for commercial material. Analyses by </span>VCD of the free amine, by NMR analysis of the derived (</span><em>S</em><span>)-O-methylmandelamides and an X-ray crystal structure of one of the mandelamides defined the specific rotation for each enantiomer.</span></p></div>","PeriodicalId":22237,"journal":{"name":"Tetrahedron, asymmetry","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2017-09-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/j.tetasy.2017.08.005","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"79176791","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":"A diversity oriented synthesis of d-erythro-sphingosine and siblings","authors":"Amrita Ghosh, Shital K. Chattopadhyay","doi":"10.1016/j.tetasy.2017.08.006","DOIUrl":"10.1016/j.tetasy.2017.08.006","url":null,"abstract":"<div><p><span>An efficient building block-based synthetic protocol has been developed for the synthesis of 3-ketosphingoids with various chain lengths using cross metathesis<span> of a Garner’s aldehyde-derived α,β-unsaturated ketone as the key step. Stereoselective reduction of the biomimetic precursors thus obtained provided </span></span><span>d</span>-<em>erythro</em>-sphingosine and truncated anaogues in good overall yields.</p></div>","PeriodicalId":22237,"journal":{"name":"Tetrahedron, asymmetry","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2017-09-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/j.tetasy.2017.08.006","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"72530377","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}
Aoife M. Foley , Declan P. Gavin , Ilona Joniec , Anita R. Maguire
{"title":"Impact of variation of the acyl group on the efficiency and selectivity of the lipase-mediated resolution of 2-phenylalkanols","authors":"Aoife M. Foley , Declan P. Gavin , Ilona Joniec , Anita R. Maguire","doi":"10.1016/j.tetasy.2017.08.002","DOIUrl":"10.1016/j.tetasy.2017.08.002","url":null,"abstract":"<div><p><span>By tuning the steric properties of the acyl group to control the efficiency and selectivity of the resolution, 2-phenyl-1-propanol </span><strong>1a</strong> was prepared by lipase-catalysed hydrolysis using a short-chain acyl group, with <em>E</em>-values of up to 66 (<em>ee</em> up to 95%). 2-Phenylbutan-1-ol <strong>1b</strong> was similarly resolved (up to 86% <em>ee</em>) using the optimised conditions, while the ester of the more sterically demanding 3-methyl-2-phenylbutan-1-ol <strong>1c</strong><span> proved resistant to enzymatic hydrolysis under these conditions.</span></p></div>","PeriodicalId":22237,"journal":{"name":"Tetrahedron, asymmetry","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2017-09-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/j.tetasy.2017.08.002","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"76435704","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}