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Iterative Assembly of Chiral Alcohols Utilizing CMMP-mediated Mitsunobu Reactions 利用cmmp介导Mitsunobu反应的手性醇的迭代组装
4区 化学
Synthesis-Stuttgart Pub Date : 2023-09-13 DOI: 10.1055/a-2175-1271
Kei Kitamura, Saki Ise, Tetsuto Tsunoda, Hiroto Kaku
{"title":"Iterative Assembly of Chiral Alcohols Utilizing CMMP-mediated Mitsunobu Reactions","authors":"Kei Kitamura, Saki Ise, Tetsuto Tsunoda, Hiroto Kaku","doi":"10.1055/a-2175-1271","DOIUrl":"https://doi.org/10.1055/a-2175-1271","url":null,"abstract":"We report herein an iterative assembly of chiral alcohol building blocks utilizing cyanomethylene trimethylphosphorane (CMMP)-mediated Mitsunobu reactions. 1,3-Benzodithiole tetraoxide (BDT) was used as the platform to prepare long-chain saturated compounds with multiple stereocenters en route to polyisoprenoid natural products. Selectively protected chiral 1,3-butanediols played a key role in iterative chain elongation for the construction of 1,5-dimethyl branched arrays with high stereocontrol.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"3 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-09-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135734387","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Recent Progress in Zweifel Olefination: An Update Zweifel烯烃研究进展
IF 2.6 4区 化学
Synthesis-Stuttgart Pub Date : 2023-09-08 DOI: 10.1055/a-2172-1386
Xin Li, Qiuling Song
{"title":"Recent Progress in Zweifel Olefination: An Update","authors":"Xin Li, Qiuling Song","doi":"10.1055/a-2172-1386","DOIUrl":"https://doi.org/10.1055/a-2172-1386","url":null,"abstract":"During the past several decades, Zweifel olefination has emerged as one of the most powerful and reliable tools for constructing C–C double bonds. This reaction features high efficiency, good versatility, nonuse of transition metals, and perfect stereospecificity, which make it superior to many other olefination methods. Since the summary of Zweifel olefination’s 50-years history was published in 2017 by Aggarwal et al., remarkable achievements have been made in terms of employing new organometallic species, proceeding through electrochemical or photochemical pathways, and furnishing new kinds of products. This short review summarizes and discusses the very recent progress in Zweifel olefination and its latest application in natural products synthesis. \u00001 Introduction \u00002 Zweifel Olefination with New Organometallic Species \u00003 Zweifel Olefination with New Migrating Groups \u00004 Electrochemical and Photocatalyzed Zweifel Olefination \u00005 New Elimination and Migration Patterns of Zweifel Olefination\u00006 Zweifel Olefination in Natural Product Synthesis \u00007 Other Reactions Involving the Zweifel Olefination Mechanism\u00008 Conclusions and Outlook\u0000\u0000","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"1 1","pages":""},"PeriodicalIF":2.6,"publicationDate":"2023-09-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"80985763","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Linked PDF of Table of Contents 链接的PDF目录
4区 化学
Synthesis-Stuttgart Pub Date : 2023-09-07 DOI: 10.1055/s-0040-1720091
{"title":"Linked PDF of Table of Contents","authors":"","doi":"10.1055/s-0040-1720091","DOIUrl":"https://doi.org/10.1055/s-0040-1720091","url":null,"abstract":"","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"28 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-09-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135047699","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Erratum - Synthesis of N -Propargyl Pyrrolylamides and Theoretical Study of Pyrrolylimide Reduction by NaBH 4 N -丙炔基吡咯酰胺的合成及nabh4还原吡咯酰亚胺的理论研究
IF 2.6 4区 化学
Synthesis-Stuttgart Pub Date : 2023-09-07 DOI: 10.1055/s-0040-1720090
Sinan Basceken
{"title":"Erratum - Synthesis of N -Propargyl Pyrrolylamides and Theoretical Study of Pyrrolylimide Reduction by NaBH 4","authors":"Sinan Basceken","doi":"10.1055/s-0040-1720090","DOIUrl":"https://doi.org/10.1055/s-0040-1720090","url":null,"abstract":"","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"70 1","pages":""},"PeriodicalIF":2.6,"publicationDate":"2023-09-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"84411865","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Bis(pinacoloto)diboran/4-phenyl pyridine system for one-pot photocatalyzed borylation and reduction of aldehyde: synthesis of tavaborole in a flow reactor 双(pinacoloto)diboran/4-苯基吡啶体系的一锅光催化硼化和醛还原:在流动反应器中合成tavaborole
IF 2.6 4区 化学
Synthesis-Stuttgart Pub Date : 2023-09-06 DOI: 10.1055/a-2169-6200
Kankanala Naveen Kumar, Mouzma Mhate, Velayutham Ravichandiran, S. Swain
{"title":"Bis(pinacoloto)diboran/4-phenyl pyridine system for one-pot photocatalyzed borylation and reduction of aldehyde: synthesis of tavaborole in a flow reactor","authors":"Kankanala Naveen Kumar, Mouzma Mhate, Velayutham Ravichandiran, S. Swain","doi":"10.1055/a-2169-6200","DOIUrl":"https://doi.org/10.1055/a-2169-6200","url":null,"abstract":"A photocatalyzed one-pot borylation of haloarene and reduction of aldehyde by cocatalysis of bis(pinacoloto)diboran/4-phenyl pyridine is reported. The reaction was carried out in a flow reactor by irradiating the reaction at 410nm, with residence time of 10 min. The method was successfully applied for the synthesis of tavaborole in a single step with 81% yield.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"2 1","pages":""},"PeriodicalIF":2.6,"publicationDate":"2023-09-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"74399390","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Reactions of Benzylboronate Nucleophiles. 苄基硼酸亲核试剂的反应。
IF 2.2 4区 化学
Synthesis-Stuttgart Pub Date : 2023-09-01 Epub Date: 2023-05-08 DOI: 10.1055/a-2072-2754
Timothy J Barker, Andrew Bogatkevich, Dallas W Crowder, Sophia G Gierszal, Jacob C Hayes, Michael R Hollerbach, Richard W Russell
{"title":"Reactions of Benzylboronate Nucleophiles.","authors":"Timothy J Barker, Andrew Bogatkevich, Dallas W Crowder, Sophia G Gierszal, Jacob C Hayes, Michael R Hollerbach, Richard W Russell","doi":"10.1055/a-2072-2754","DOIUrl":"10.1055/a-2072-2754","url":null,"abstract":"<p><p>This short review summarizes our laboratory's development of benzylboronic esters as nucleophiles. Activation of the benzylboronic ester is achieved by irreversible coordination of an alkyllithium Lewis base to form a nucleophilic benzylboronate. This boronate was found to react with aldehydes, imines, ketones and alkyl bromides. A copper catalyst was employed in reactions of the boronate with epoxides and aziridines.</p>","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"55 17","pages":"2639-2647"},"PeriodicalIF":2.2,"publicationDate":"2023-09-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10545366/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"41171502","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Linked PDF of Table of Contents 链接的PDF目录
4区 化学
Synthesis-Stuttgart Pub Date : 2023-08-29 DOI: 10.1055/s-0040-1720089
{"title":"Linked PDF of Table of Contents","authors":"","doi":"10.1055/s-0040-1720089","DOIUrl":"https://doi.org/10.1055/s-0040-1720089","url":null,"abstract":"","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"26 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-08-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"136243301","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Erratum - Synthesis and Optical Resolution of Inherently Chiral Fluorescent Calix[4]arenes and Their Application in Chiral Recognition 固有手性荧光杯[4]芳烃的合成、光学分辨及其在手性识别中的应用
IF 2.6 4区 化学
Synthesis-Stuttgart Pub Date : 2023-08-17 DOI: 10.1055/s-0040-1720085
Fu Yang, Jun Luo, Yi-Chieh Chen, W. Chung
{"title":"Erratum - Synthesis and Optical Resolution of Inherently Chiral Fluorescent Calix[4]arenes and Their Application in Chiral Recognition","authors":"Fu Yang, Jun Luo, Yi-Chieh Chen, W. Chung","doi":"10.1055/s-0040-1720085","DOIUrl":"https://doi.org/10.1055/s-0040-1720085","url":null,"abstract":"","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"42 2 1","pages":"e1 - e1"},"PeriodicalIF":2.6,"publicationDate":"2023-08-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"84113399","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Heteroatom-Embedding Annulative π-Extension (Hetero-APEX) Reactions: An Overview 杂原子包埋环性π扩展反应综述
IF 2.6 4区 化学
Synthesis-Stuttgart Pub Date : 2023-08-17 DOI: 10.1055/a-2169-4078
Hideto Ito, Kou P Kawahara, Kenichiro Itami
{"title":"Heteroatom-Embedding Annulative π-Extension (Hetero-APEX) Reactions: An Overview","authors":"Hideto Ito, Kou P Kawahara, Kenichiro Itami","doi":"10.1055/a-2169-4078","DOIUrl":"https://doi.org/10.1055/a-2169-4078","url":null,"abstract":"Heteroatom-embedded polycyclic aromatic compounds (hetero-PACs) are a class of organic compounds contributing to a variety of research fields such as materials science, chemical biology and so on. For applications using hetero-PACs, efficient preparation of hetero-PACs is essential. In particular, reactions transforming unfunctionalized aromatic compounds to hetero-PACs using appropriate heteroatom-containing aromatic compounds (π-extending agents) represent the most ideal way to prepare hetero-PACs. In this review, such heteroatom-embedding annulative π-extension (hetero-APEX) reactions including their reaction mechanisms and scope of substrates are described.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"798 1","pages":""},"PeriodicalIF":2.6,"publicationDate":"2023-08-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"85445000","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 1
Linked PDF of Table of Contents 链接的PDF目录
4区 化学
Synthesis-Stuttgart Pub Date : 2023-08-15 DOI: 10.1055/s-0040-1720083
{"title":"Linked PDF of Table of Contents","authors":"","doi":"10.1055/s-0040-1720083","DOIUrl":"https://doi.org/10.1055/s-0040-1720083","url":null,"abstract":"","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"10 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-08-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135065281","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
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