Sasirome Racochote, Prof. Dr. Chutima Kuhakarn, Dr. Pawaret Leowanawat, Dr. Khetpakorn Chakarawet, Prof. Dr. Vichai Reutrakul, Dr. Darunee Soorukram
{"title":"Front Cover: Synthesis of Chiral β-Trifluoromethyl-β-Amino Acid Derivatives in Aqueous Medium (Asian J. Org. Chem. 4/2025)","authors":"Sasirome Racochote, Prof. Dr. Chutima Kuhakarn, Dr. Pawaret Leowanawat, Dr. Khetpakorn Chakarawet, Prof. Dr. Vichai Reutrakul, Dr. Darunee Soorukram","doi":"10.1002/ajoc.202580401","DOIUrl":"https://doi.org/10.1002/ajoc.202580401","url":null,"abstract":"<p>In article number e202400812, Darunee Soorukram and co-workers report a practical process to perform diastereoselective aza-Michael addition of aromatic amines to chiral Michael substrate using water as a reaction medium leading to the synthesis of enantioenriched <i>β</i>-trifluoromethyl-<i>β</i>-amino acid derivatives. It has been observed that the reaction proceeded at an accelerated rate when conducted in water (in comparison to organic solvents). Therefore, the cover of this work is designed to highlight the key feature of using water as a solvent, which is safe, cost-effective, and environmentally friendly, for conducting stereoselective organic reactions. A fishing hook is used as a representative of the hydrogen bond between chiral substrate and water or amine, which plays a significant role in influencing the face-selectivity of the reactions.\u0000 <figure>\u0000 <div><picture>\u0000 <source></source></picture><p></p>\u0000 </div>\u0000 </figure>\u0000 </p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 4","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-04-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ajoc.202580401","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143846069","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}
{"title":"RETRACTION: RETRACTION: Copper-Mediated (2-Methylthio)aniline Directed Annulation of sp2 C−H Bonds with Primary Anilines","authors":"","doi":"10.1002/ajoc.202500189","DOIUrl":"https://doi.org/10.1002/ajoc.202500189","url":null,"abstract":"<p><b>RETRACTION</b>: K. M. Tran, N. T. Ho, T. T. T. Le, T.T. Nguyen, and N. T. S. Phan, “Copper-Mediated (2-Methylthio)aniline Directed Annulation of sp<sup>2</sup> C−H Bonds with Primary Anilines,” <i>Asian J. Org. Chem</i>. (Early View): https://doi.org/10.1002/ajoc.202100434.</p><p>The above article, published online on 16 July 2021 in Wiley Online Library (wileyonlinelibrary.com), has been retracted by agreement between the journal Editor, Dr. Dörthe Mellmann; journal Editor-in-Chief Dr. Dinesh Talwar; and Wiley-VCH GmbH. Following publication as an Accepted Article, multiple third parties raised concerns over the origin and veracity of the data included in the article. The journal contacted the authors to ask for the original data and a response to these concerns. Although the authors eventually responded and provided data, their explanation did not adequately address the original concerns. The retraction has been agreed to because the data reported in this article do not meet the reporting requirements set by the journal and because the validity of the data could not be determined. The authors disagree with the retraction.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 4","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-04-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ajoc.202500189","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143845796","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}
{"title":"Arylation of α‐Imino Ketones and their Cyclization with Allenoates: Direct Access to Sterically Hindered Pyrroles","authors":"Srinivasarao Yaragorla , Doma Arun","doi":"10.1002/ajoc.202400756","DOIUrl":"10.1002/ajoc.202400756","url":null,"abstract":"<div><div>Herein, we report a calcium‐catalyzed, one‐pot, four‐component reaction to synthesize diversely substituted pyrroles. This atom‐economy reaction involves a sequence of reactions that proceed via in situ formation of α ‐ imino ketones, Friedel‐Crafts arylation, aza‐cyclization, and aromatization in the single pot. The reaction showed a broad substrate scope with good yields. We demonstrated the gram‐scale synthesis and post‐synthetic modifications.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 4","pages":"Article e202400756"},"PeriodicalIF":2.8,"publicationDate":"2025-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143846149","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}
Mamta , Imtiyaz Ahmad Shah , Mainika Verma , Prof. Krishnan Rangan , Prof. Eldhose Iype , Prof. Bharti Khungar , Prof. Indresh Kumar
{"title":"Two‐Pot Synthesis of Indolizinoindole Derivatives via Lewis Acid‐Mediated Intramolecular Regioselective Cyclization of 3‐Acylpyrroles","authors":"Mamta , Imtiyaz Ahmad Shah , Mainika Verma , Prof. Krishnan Rangan , Prof. Eldhose Iype , Prof. Bharti Khungar , Prof. Indresh Kumar","doi":"10.1002/ajoc.202400733","DOIUrl":"10.1002/ajoc.202400733","url":null,"abstract":"<div><div>A two‐pot method has been developed to access indolizino[8,7‐<em>b</em>]indole derivatives through Lewis acid‐mediated regioselective C5‐cyclization of 3‐acylpyrrole prepared from the feedstock materials. The overall reaction proceeds through amine‐catalyzed direct aldol reaction/Paal‐Knorr reaction/oxidation between succinaldehyde, aromatic aldehyde, and tryptamine in a sequential multicomponent fashion for N‐alkyl pyrrole followed by dearomative cyclization. A series of substituted indolizino[8,7‐<em>b</em>]indoles have been prepared with good yields and excellent regioselectivity.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 4","pages":"Article e202400733"},"PeriodicalIF":2.8,"publicationDate":"2025-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143845941","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}
Yujiro Hayashi , Hinata Odaira , Masashi Tomikawa , Naoki Mori , Tohru Taniguchi , Kenji Monde
{"title":"Enantioselective Synthesis of α‐Trifluoromethyl tert‐Alcohols and Amines via Organocatalyst‐Mediated Aldol and Mannich Reactions","authors":"Yujiro Hayashi , Hinata Odaira , Masashi Tomikawa , Naoki Mori , Tohru Taniguchi , Kenji Monde","doi":"10.1002/ajoc.202500035","DOIUrl":"10.1002/ajoc.202500035","url":null,"abstract":"<div><div>The asymmetric aldol reaction of ethyl trifluoropyruvate with aldehydes was developed using diarylprolinol as a catalyst, affording α‐trifluoromethyl‐substituted tertiary alcohols with high enantioselectivity. Similarly, the asymmetric Mannich reaction of aldehydes with an imine derived from ethyl trifluoropyruvate was developed using diphenylprolinol silyl ether in combination with an acid, yielding α‐trifluoromethyl‐substituted tertiary amines. The absolute and relative configurations of the products were determined by vibrational circular dichroism (VCD).</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 4","pages":"Article e202500035"},"PeriodicalIF":2.8,"publicationDate":"2025-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143845861","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}
{"title":"Switchable Site‐Selectivite Direct Acetoxylation of Pyrazolones","authors":"Tanakorn Kittikool , Tarm Viriyanukul , Kunita Phakdeeyothin , Sirilata Yotphan","doi":"10.1002/ajoc.202400808","DOIUrl":"10.1002/ajoc.202400808","url":null,"abstract":"<div><div>Site‐selective direct acetoxylation of pyrazolones was accomplished by utilizing an easy‐to‐handle (diacetoxyiodo)benzene (PIDA) as the sole acetoxylating reagent. In the presence of Pd(OAc)<sub>2</sub> catalyst, the 4‐acetoxylated pyrazolone product was exclusively formed. Meanwhile, in the absence of Pd(OAc)<sub>2</sub>, the pyrazolone methyl acetate product was obtained over the C<em>sp</em><sup><em>2</em></sup>−H bond functionalization. Both approaches have been successfully applied to various pyrazolone substrates, giving the corresponding products in moderate to high yields under mild conditions.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 4","pages":"Article e202400808"},"PeriodicalIF":2.8,"publicationDate":"2025-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143845934","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}
Melinda Nonn , Róbert Berkecz , Santos Fustero , Ágnes Lackfi , Gábor Hornyánszky , Loránd Kiss
{"title":"Studies on the Synthesis of Some Functionalized Azaheterocycles through Oxidative Ring Opening/Ring Closing by Reductive Amination","authors":"Melinda Nonn , Róbert Berkecz , Santos Fustero , Ágnes Lackfi , Gábor Hornyánszky , Loránd Kiss","doi":"10.1002/ajoc.202400818","DOIUrl":"10.1002/ajoc.202400818","url":null,"abstract":"<div><div>Selected functionalized saturated azaheterocycles have been prepared by ring expansion from various cycloalkene derivatives involving oxidative ring opening/ring closing by reductive amination. Studies have been conducted regarding the outcome of the transformations, the effect of the ring strain, and stereocontrol. The synthesized amino acid derivatives possessing either an aryl or fluorine element in their structure might be relevant building blocks for foldamer chemistry.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 4","pages":"Article e202400818"},"PeriodicalIF":2.8,"publicationDate":"2025-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143846026","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}
Prof. Wei Ma , Qiang Zhao , Shibin Su , Weiwei Zhang , Yao Yao , Pei Wang , Dr. Dong Tang , Dr. Pengjuan Zhou
{"title":"Ruthenium‐catalyzed reaction of dinitriles with primary alcohols for the synthesis of N‐alkylated cyclic β‐enaminonitriles","authors":"Prof. Wei Ma , Qiang Zhao , Shibin Su , Weiwei Zhang , Yao Yao , Pei Wang , Dr. Dong Tang , Dr. Pengjuan Zhou","doi":"10.1002/ajoc.202400730","DOIUrl":"10.1002/ajoc.202400730","url":null,"abstract":"<div><div>A novel one‐pot synthetic approach for preparing N‐alkylated cyclic β‐enaminonitriles has been developed using readily available aliphatic dinitriles and primary alcohols. This method utilizes a Ru‐MACHO complex catalyst (1 mol%) in conjunction with a strong base and a nonpolar solvent, exhibiting a broad substrate scope and excellent functional group tolerance. The process is highly atom economic, producing water as the sole by‐produc. A range of N‐alkylated cyclic β‐enaminonitriles were synthesized in good to excellent yields, and the method was successfully scaled up to gram‐scale synthesis.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 4","pages":"Article e202400730"},"PeriodicalIF":2.8,"publicationDate":"2025-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143845823","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}
Nitchakan Purahong , Dr. Thapong Teerawatananond , Dr. Nawasit Chotsaeng , Pattarapapa Janthakit , Phattananawee Nalaoh , Prof. Dr. Vinich Promarak , Prof. Dr. Chutima Kuhakarn , Dr. Jatuporn Meesin
{"title":"DBU‐Mediated Reaction of 3‐Chlorooxindole and 9‐Xanthyl Fluorene for Synthesis of 3‐Arylidene Oxindole","authors":"Nitchakan Purahong , Dr. Thapong Teerawatananond , Dr. Nawasit Chotsaeng , Pattarapapa Janthakit , Phattananawee Nalaoh , Prof. Dr. Vinich Promarak , Prof. Dr. Chutima Kuhakarn , Dr. Jatuporn Meesin","doi":"10.1002/ajoc.202400660","DOIUrl":"10.1002/ajoc.202400660","url":null,"abstract":"<div><div>This work reports a new route for the synthesis of 3‐(9<em>H</em>‐fluoren‐9‐ylidene)indolin‐2‐one derivatives via the reaction of 3‐chlorooxindoles and <em>O</em>‐ethyl <em>S</em>‐(9<em>H</em>‐fluoren‐9‐yl) carbonodithioates mediated by 1,8‐diazabicyclo[5.4.0]undec‐7‐ene (DBU). The reactions readily proceeded at room temperature, enable a collection of 3‐alkenyl oxindoles to be prepared within a short reaction time (15 minutes). The 3‐alkenyl oxindoles can be easily converted to 3‐fluorenyl oxindoles by NaBH<sub>4</sub> reduction.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 4","pages":"Article e202400660"},"PeriodicalIF":2.8,"publicationDate":"2025-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143845860","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}
Liting Yang , Xinyu Cao , Xiaoxu Xu , Hao Zheng , Shuyu Lai , Sicheng Chen , Jinyu Wang , Xilin Zhu , Yanjie Wang , Xiangtao Kong , Huijie Qiao , Mingli Jiao
{"title":"Direct C3−H Amination of Imidazo[1,2‐a]Pyridine under Simple and Mild Conditions","authors":"Liting Yang , Xinyu Cao , Xiaoxu Xu , Hao Zheng , Shuyu Lai , Sicheng Chen , Jinyu Wang , Xilin Zhu , Yanjie Wang , Xiangtao Kong , Huijie Qiao , Mingli Jiao","doi":"10.1002/ajoc.202400718","DOIUrl":"10.1002/ajoc.202400718","url":null,"abstract":"<div><div>This paper reports a simple and efficient method for the direct regioselective C3−H amination of imidazo[1,2‐a]pyridine derivatives using diphenylsulfonimide as the amination source and PhI(OAc)<sub>2</sub> as the oxidant. The proposed conversion protocol, which is characterized by mild and safe reaction conditions (room temperature reaction), simple execution (catalyst‐free, transition‐metal‐free, and additive‐free), and broad substrate applicability, enables the synthesis of 3‐sulfonamido‐imidazo[1,2‐a]pyridine derivatives with a wide range of functional groups. Controlled experiments and theoretical calculations indicate that the amination occurs at the C3 position through a radical mechanism. In addition, a series of indole derivatives could also be used in this amination system. This study could guide future research on green organic synthesis, which has immense industrial and academic value.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 4","pages":"Article e202400718"},"PeriodicalIF":2.8,"publicationDate":"2025-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143845929","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}