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One-Pot Production of Cinnamonitriles from Lignin β-O-4 Segments Induced by Selective Oxidation of the γ-OH Group
IF 3.3 2区 化学
Journal of Organic Chemistry Pub Date : 2024-12-10 DOI: 10.1021/acs.joc.4c0231110.1021/acs.joc.4c02311
Qian Qiang, Qi Luo, Hua Wang, Shenglong Tian, Wentao Su, Haiyan He, Huamei Yang, Changzhi Li* and Tao Zhang*, 
{"title":"One-Pot Production of Cinnamonitriles from Lignin β-O-4 Segments Induced by Selective Oxidation of the γ-OH Group","authors":"Qian Qiang,&nbsp;Qi Luo,&nbsp;Hua Wang,&nbsp;Shenglong Tian,&nbsp;Wentao Su,&nbsp;Haiyan He,&nbsp;Huamei Yang,&nbsp;Changzhi Li* and Tao Zhang*,&nbsp;","doi":"10.1021/acs.joc.4c0231110.1021/acs.joc.4c02311","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02311https://doi.org/10.1021/acs.joc.4c02311","url":null,"abstract":"<p >The construction of N-containing aromatic compounds from lignin is of great importance to expanding the boundary of the biorefinery and meeting the demand for value-added biorefinery. However, it remains a huge challenge due to the complex lignin structure and the incompatible catalysis for C–O/C–C bond cleavage and C–N formation. Herein, sustainable synthesis of cinnamonitrile derivatives from lignin β-O-4 model compounds in the presence of 2,2,6,6-tetramethylpiperidine oxide (TEMPO), (diacetoxyiodo)benzene (BAIB), and a strong base has been achieved in a one-pot, two-step fashion under transition-metal-free conditions. Mechanistic studies suggest that this transformation starts from selective oxidation of C<sub>γ</sub>-OH of the β-O-4 model compound, followed by retro-aldol condensation, resulting in the cleavage of the C<sub>α</sub>–C<sub>β</sub> bond to afford veratraldehyde. Whereafter, the aldol condensation reaction allows coupling of veratraldehyde with nitriles to provide cinnamonitriles. With this protocol, 3,4-dimethoxycinnamonitrile and 3,4-dimethoxyphenyl-2-phenylacrylonitrile were synthesized from lignin β-O-4 model compounds and showed good antibacterial or antifungal activity, showcasing the application potential of lignin in pharmaceutical synthesis.</p>","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"89 24","pages":"18424–18435 18424–18435"},"PeriodicalIF":3.3,"publicationDate":"2024-12-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142858630","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
One-Step Regioselective Synthesis of N-1-Substituted Dihydrouracils: A Motif of Growing Popularity in the Targeted Protein Degradation Field
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2024-12-10 DOI: 10.1021/acs.joc.4c02136
Ian D. G. Nixon, Joseph M. Bateman, Iacovos N. Michaelides, Gary Fairley, Miles J. Pemberton, Erin L. Braybrooke, Kyran Sutton, Peter J. Lindsay-Scott
{"title":"One-Step Regioselective Synthesis of N-1-Substituted Dihydrouracils: A Motif of Growing Popularity in the Targeted Protein Degradation Field","authors":"Ian D. G. Nixon, Joseph M. Bateman, Iacovos N. Michaelides, Gary Fairley, Miles J. Pemberton, Erin L. Braybrooke, Kyran Sutton, Peter J. Lindsay-Scott","doi":"10.1021/acs.joc.4c02136","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02136","url":null,"abstract":"The increasing popularity of the dihydrouracil motif in cereblon (CRBN) recruiting proteolysis-targeting chimeras (PROTACs) has necessitated the development of a facile, cost-effective, and high-yielding method for its introduction into molecules. To that end, we disclose herein an N-1 selective Pd-catalyzed cross-coupling of dihydrouracil with aryl electrophiles to provide access to medicinally relevant scaffolds in a single step. This approach exhibits excellent functional group tolerance and broad applicability to an abundance of (hetero)aryl halides and phenol derivatives and utilizes readily available catalyst/ligand systems. Thus, our strategy should find broad utility in the arena of PROTAC research, as it obviates the drawbacks of previous methodologies that rely on multistep synthetic routes and protecting group strategies to achieve N-1 selectivity.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"52 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2024-12-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142797776","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Redox Active vs Redox Neutral in Ru/Pd-Catalyzed Sulfonylation: Theoretical Insights into Structure–Activity Relationship between Metal Centers and Regio-Selectivity
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2024-12-10 DOI: 10.1021/acs.joc.4c01940
Qingqing Lin, Huan Lv, Yu Lu, Chengkai Yang, Yan Yu, Zheyuan Liu
{"title":"Redox Active vs Redox Neutral in Ru/Pd-Catalyzed Sulfonylation: Theoretical Insights into Structure–Activity Relationship between Metal Centers and Regio-Selectivity","authors":"Qingqing Lin, Huan Lv, Yu Lu, Chengkai Yang, Yan Yu, Zheyuan Liu","doi":"10.1021/acs.joc.4c01940","DOIUrl":"https://doi.org/10.1021/acs.joc.4c01940","url":null,"abstract":"The structure–activity relationship between the metal center and regio-selectivity is persistently a pivotal scientific issue. To address this, we select the 2-phenylpyridine sulfonylation reactions catalyzed by ruthenium and palladium as research subjects. An extensive theoretical study has been conducted on their reaction mechanisms, the sources of regio-selectivity, and the evolution of electronic structures. The distinct electronic structures lead to completely different catalytic mechanisms and electronic structure evolution processes for ruthenium and palladium. Ruthenium tends to form six-coordinate octahedral complexes, thus undergoing an inner-sphere redox active Ru(II)–Ru(III)–Ru(IV)–Ru(II) catalytic cycle. In contrast, palladium tends to form four-coordinate planar quadrilateral complexes, hence undergoing an outer-sphere redox neutral Pd(II) catalytic cycle. The distinct electronic structure evolution processes fundamentally differentiate the radical attack modes in the sulfonation process, thereby determining the regio-selectivity of the reaction. In the Ru-catalyzed system, the meta-selectivity arises mainly from a more stable Schrock carbene-type meta-intermediate. For the Pd-catalyzed system, the ortho-selectivity mainly comes from the stabilizing effect of the Pd(II) center on the single electron. This study provides novel insights into how the electronic structure of metal centers influences the reaction mechanism and selectivity, making a theoretical contribution to a deeper comprehension of the mechanism and regio-selectivity underlying aromatic functionalization reactions.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"28 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2024-12-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142805039","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Application of β-Keto Acylpyrazoles as 2C Synthons in Asymmetric Cyclizations of ortho-Hydroxychalcones: Stereoselective Construction of trans-3,4-Dihydrocoumarins
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2024-12-10 DOI: 10.1021/acs.joc.4c01327
Liying Cui, Xiaofeng Yang, Changchun Yuan, Zhenghong Zhou
{"title":"Application of β-Keto Acylpyrazoles as 2C Synthons in Asymmetric Cyclizations of ortho-Hydroxychalcones: Stereoselective Construction of trans-3,4-Dihydrocoumarins","authors":"Liying Cui, Xiaofeng Yang, Changchun Yuan, Zhenghong Zhou","doi":"10.1021/acs.joc.4c01327","DOIUrl":"https://doi.org/10.1021/acs.joc.4c01327","url":null,"abstract":"An asymmetric tandem esterification/Michael addition reaction of β-keto acylpyrazoles with <i>o</i>-hydroxychalcones has been established under the catalysis of a bifunctional squaramide-tertiary amine. A wide variety of biorelevant 3,4-dihydrocoumarin derivatives were generally obtained in high yields (up to 93%) with excellent diastereo- and enantioselectivities (&gt;19:1 dr, up to 93% ee) under mild reaction conditions. This reaction represents the successful application of β-keto acylpyrazoles as 2C building blocks in catalytic asymmetric cyclizations.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"29 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2024-12-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142797773","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Palladium-Catalyzed Tandem Cyclization of Functional Diarylalkynes and Isocyanides for the Assembly of Isochromeno[4,3-c]quinolines 钯催化功能性二芳基炔和异氰酸酯的串联环化以组装异色烯并[4,3-c]喹啉类化合物
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2024-12-10 DOI: 10.1021/acs.joc.4c02142
Qiushan Gao, Binbin Wang, Huanfeng Jiang, Wanqing Wu
{"title":"Palladium-Catalyzed Tandem Cyclization of Functional Diarylalkynes and Isocyanides for the Assembly of Isochromeno[4,3-c]quinolines","authors":"Qiushan Gao, Binbin Wang, Huanfeng Jiang, Wanqing Wu","doi":"10.1021/acs.joc.4c02142","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02142","url":null,"abstract":"A novel strategy for the synthesis of various isochromeno[4,3-<i>c</i>]quinolines via palladium-catalyzed tandem cyclization of functional diarylalkynes with isocyanides has been developed. This approach features excellent chemo- and regioselectivities as well as good functional group tolerance. Notably, 6-phenylimino-6<i>H</i>-isochromeno[4,3-<i>c</i>]quinolin-11-amines and 11-amino-6<i>H</i>-isochromeno[4,3-<i>c</i>]quinolin-6-ones can be selectively constructed by employing different protecting groups of functional diarylalkynes. The gram-scale and late-stage modifications further demonstrate the synthetic value of this method.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"95 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2024-12-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142797777","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Multigram Synthesis of 3,3-Spiro-α-prolines
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2024-12-10 DOI: 10.1021/acs.joc.4c02019
Nikita O. Derkach, Kostiantyn V. Levchenko, Ievgenii A. Iermolenko, Eugeniy N. Ostapchuk, Dmitry A. Lega, Valeriya G. Makhankova, Alexander B. Rozhenko, Dmytro M. Volochnyuk, Serhiy V. Ryabukhin
{"title":"Multigram Synthesis of 3,3-Spiro-α-prolines","authors":"Nikita O. Derkach, Kostiantyn V. Levchenko, Ievgenii A. Iermolenko, Eugeniy N. Ostapchuk, Dmitry A. Lega, Valeriya G. Makhankova, Alexander B. Rozhenko, Dmytro M. Volochnyuk, Serhiy V. Ryabukhin","doi":"10.1021/acs.joc.4c02019","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02019","url":null,"abstract":"A series of novel spirocyclic α-proline building blocks with a spiro conjunction in position 3 of the pyrrolidine ring was prepared to employ two convenient and practical synthetic approaches. Both alternative routes utilize simple and readily available starting materials─cyclic ketones and esters─and comprise 6 and 7 steps, respectively. The methodologies feature distinct advantages, using routine organic chemistry transformations, and are suitable for producing multigram amounts of the target prolines. The approach also became valuable for spirocyclic pyroglutamic acids.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"93 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2024-12-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142797775","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Palladium-Catalyzed Tandem Cyclization of Functional Diarylalkynes and Isocyanides for the Assembly of Isochromeno[4,3-c]quinolines 钯催化功能性二芳基炔和异氰酸酯的串联环化以组装异色烯并[4,3-c]喹啉类化合物
IF 3.3 2区 化学
Journal of Organic Chemistry Pub Date : 2024-12-10 DOI: 10.1021/acs.joc.4c0214210.1021/acs.joc.4c02142
Qiushan Gao, Binbin Wang, Huanfeng Jiang and Wanqing Wu*, 
{"title":"Palladium-Catalyzed Tandem Cyclization of Functional Diarylalkynes and Isocyanides for the Assembly of Isochromeno[4,3-c]quinolines","authors":"Qiushan Gao,&nbsp;Binbin Wang,&nbsp;Huanfeng Jiang and Wanqing Wu*,&nbsp;","doi":"10.1021/acs.joc.4c0214210.1021/acs.joc.4c02142","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02142https://doi.org/10.1021/acs.joc.4c02142","url":null,"abstract":"<p >A novel strategy for the synthesis of various isochromeno[4,3-<i>c</i>]quinolines via palladium-catalyzed tandem cyclization of functional diarylalkynes with isocyanides has been developed. This approach features excellent chemo- and regioselectivities as well as good functional group tolerance. Notably, 6-phenylimino-6<i>H</i>-isochromeno[4,3-<i>c</i>]quinolin-11-amines and 11-amino-6<i>H</i>-isochromeno[4,3-<i>c</i>]quinolin-6-ones can be selectively constructed by employing different protecting groups of functional diarylalkynes. The gram-scale and late-stage modifications further demonstrate the synthetic value of this method.</p>","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"89 24","pages":"18370–18383 18370–18383"},"PeriodicalIF":3.3,"publicationDate":"2024-12-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142867881","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
One-Pot Production of Cinnamonitriles from Lignin β-O-4 Segments Induced by Selective Oxidation of the γ-OH Group 通过选择性氧化γ-OH基团诱导从木质素β-O-4段单锅生产肉桂三烯烃
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2024-12-10 DOI: 10.1021/acs.joc.4c02311
Qian Qiang, Qi Luo, Hua Wang, Shenglong Tian, Wentao Su, Haiyan He, Huamei Yang, Changzhi Li, Tao Zhang
{"title":"One-Pot Production of Cinnamonitriles from Lignin β-O-4 Segments Induced by Selective Oxidation of the γ-OH Group","authors":"Qian Qiang, Qi Luo, Hua Wang, Shenglong Tian, Wentao Su, Haiyan He, Huamei Yang, Changzhi Li, Tao Zhang","doi":"10.1021/acs.joc.4c02311","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02311","url":null,"abstract":"The construction of N-containing aromatic compounds from lignin is of great importance to expanding the boundary of the biorefinery and meeting the demand for value-added biorefinery. However, it remains a huge challenge due to the complex lignin structure and the incompatible catalysis for C–O/C–C bond cleavage and C–N formation. Herein, sustainable synthesis of cinnamonitrile derivatives from lignin β-O-4 model compounds in the presence of 2,2,6,6-tetramethylpiperidine oxide (TEMPO), (diacetoxyiodo)benzene (BAIB), and a strong base has been achieved in a one-pot, two-step fashion under transition-metal-free conditions. Mechanistic studies suggest that this transformation starts from selective oxidation of C<sub>γ</sub>-OH of the β-O-4 model compound, followed by retro-aldol condensation, resulting in the cleavage of the C<sub>α</sub>–C<sub>β</sub> bond to afford veratraldehyde. Whereafter, the aldol condensation reaction allows coupling of veratraldehyde with nitriles to provide cinnamonitriles. With this protocol, 3,4-dimethoxycinnamonitrile and 3,4-dimethoxyphenyl-2-phenylacrylonitrile were synthesized from lignin β-O-4 model compounds and showed good antibacterial or antifungal activity, showcasing the application potential of lignin in pharmaceutical synthesis.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"7 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2024-12-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142797781","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Application of β-Keto Acylpyrazoles as 2C Synthons in Asymmetric Cyclizations of ortho-Hydroxychalcones: Stereoselective Construction of trans-3,4-Dihydrocoumarins β-酮酰基吡唑作为 2C 合成子在正羟基查耳酮不对称环化中的应用：反式-3,4-二氢香豆素的立体选择性构建
IF 3.3 2区 化学
Journal of Organic Chemistry Pub Date : 2024-12-10 DOI: 10.1021/acs.joc.4c0132710.1021/acs.joc.4c01327
Liying Cui*, Xiaofeng Yang, Changchun Yuan and Zhenghong Zhou*, 
{"title":"Application of β-Keto Acylpyrazoles as 2C Synthons in Asymmetric Cyclizations of ortho-Hydroxychalcones: Stereoselective Construction of trans-3,4-Dihydrocoumarins","authors":"Liying Cui*,&nbsp;Xiaofeng Yang,&nbsp;Changchun Yuan and Zhenghong Zhou*,&nbsp;","doi":"10.1021/acs.joc.4c0132710.1021/acs.joc.4c01327","DOIUrl":"https://doi.org/10.1021/acs.joc.4c01327https://doi.org/10.1021/acs.joc.4c01327","url":null,"abstract":"<p >An asymmetric tandem esterification/Michael addition reaction of β-keto acylpyrazoles with <i>o</i>-hydroxychalcones has been established under the catalysis of a bifunctional squaramide-tertiary amine. A wide variety of biorelevant 3,4-dihydrocoumarin derivatives were generally obtained in high yields (up to 93%) with excellent diastereo- and enantioselectivities (&gt;19:1 dr, up to 93% ee) under mild reaction conditions. This reaction represents the successful application of β-keto acylpyrazoles as 2C building blocks in catalytic asymmetric cyclizations.</p>","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"89 24","pages":"17950–17959 17950–17959"},"PeriodicalIF":3.3,"publicationDate":"2024-12-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142867868","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Solvent-Controlled Diastereodivergent Synthesis of Hexahydropyrrolo[2,1-a]isoquinolines through Pd/C-Catalyzed Dehydrogenative [3 + 2] Cycloaddition
IF 3.3 2区 化学
Journal of Organic Chemistry Pub Date : 2024-12-10 DOI: 10.1021/acs.joc.4c0234310.1021/acs.joc.4c02343
Ji-Chao Lu, Hao Bai, Yue-He Huang, Zhen-Yu Wang, Lan-Jun Cheng*, You-Gui Li and Xiang Wu*, 
{"title":"Solvent-Controlled Diastereodivergent Synthesis of Hexahydropyrrolo[2,1-a]isoquinolines through Pd/C-Catalyzed Dehydrogenative [3 + 2] Cycloaddition","authors":"Ji-Chao Lu,&nbsp;Hao Bai,&nbsp;Yue-He Huang,&nbsp;Zhen-Yu Wang,&nbsp;Lan-Jun Cheng*,&nbsp;You-Gui Li and Xiang Wu*,&nbsp;","doi":"10.1021/acs.joc.4c0234310.1021/acs.joc.4c02343","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02343https://doi.org/10.1021/acs.joc.4c02343","url":null,"abstract":"<p >A Pd/C-catalyzed dehydrogenative [3 + 2] cycloaddition is described for the diastereoswitchable synthesis of hexahydropyrrolo[2,1-<i>a</i>]isoquinolines by altering solvents. The reaction proceeds through a sequential Pd/C-catalyzed dehydrogenative formation of azomethine ylides from tetrahydroisoquinoline acetates and 1,3-dipolar cycloaddition with 2-nitroethenylbenzenes. This method displayed tunable diastereoselectivity, a broad substrate scope and good functional group compatibility. Moreover, a gram-scale synthesis and selective reductive or oxidative transformations of the product further demonstrate the utility of this methodology.</p>","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"89 24","pages":"18723–18728 18723–18728"},"PeriodicalIF":3.3,"publicationDate":"2024-12-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142858632","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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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