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Ex-Chiral-pool Synthesis of Optically Active 4-Alkylidene-Tetrahydroisoquinolines – Key Intermediates for Crinane Alkaloid Total Syntheses 具有光学活性的 4-亚烷基四氢异喹啉的手性池外合成--铬烷类生物碱全合成的关键中间体
Synthesis Pub Date : 2024-05-15 DOI: 10.1055/a-2328-2947
Stefan Bernhard, Nadine Kümmerer, Dagmar Urgast, Frederik Hack, Julia Ungelenk, Andrea Frank, Dieter Schollmeyer, Udo Nubbemeyer
{"title":"Ex-Chiral-pool Synthesis of Optically Active 4-Alkylidene-Tetrahydroisoquinolines – Key Intermediates for Crinane Alkaloid Total Syntheses","authors":"Stefan Bernhard, Nadine Kümmerer, Dagmar Urgast, Frederik Hack, Julia Ungelenk, Andrea Frank, Dieter Schollmeyer, Udo Nubbemeyer","doi":"10.1055/a-2328-2947","DOIUrl":"https://doi.org/10.1055/a-2328-2947","url":null,"abstract":"A seven-step ex-chiral-pool synthesis of optically active 4-alkylidene-tetrahydroisoquinolines was developed. Starting from 6-bromopiperonal and (S)-serine esters N-benzylation via reductive amination gave enantiopure N-piperonyl serine esters. Subsequent NH and OH protection delivered defined (S)-serine building blocks. Best results to achieve the conversion into the corresponding serinal were obtained via a two-step sequence of NaBH4/LiCl reduction and subsequent TEMPO oxidation. Then, chain elongation using the Masamune-Roush variant of the Horner olefination afforded (E)-ethyl 4-(N-6-bromopiperonyl) substituted pentenoates with high yields. Intramolecular Heck cyclization employing the Herrmann-Beller catalyst enabled generation of enantiopure 4-(2-ethoxycarbonylmethylidene)-tetrahydroisoquinoline building blocks with high (Z) selectivity. Subsequent selected functional group transformations gave carbinols and lactones, which will be used as key intermediates in crinane alkaloid total syntheses.","PeriodicalId":510101,"journal":{"name":"Synthesis","volume":"61 21","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-05-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140975134","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}
引用次数: 0
Palladium nano-dispersed and stabilized in organically modified silicate as a heterogenous catalyst for the conversion of aldehydes into O-silyl ether derivatives under neat conditions. 纳米分散并稳定在有机改性硅酸盐中的钯作为一种异源催化剂，用于在纯净条件下将醛转化为 O-硅醚衍生物。
Synthesis Pub Date : 2024-05-14 DOI: 10.1055/a-2326-6277
Caitlyn M. Matherne, Jordan E. Wroblewski, Heather S Drago, Gabriela T Marchan, Alexis R Young, Nkechi Kingsley, Craig P. Plaisance, J. Fotie
{"title":"Palladium nano-dispersed and stabilized in organically modified silicate as a heterogenous catalyst for the conversion of aldehydes into O-silyl ether derivatives under neat conditions.","authors":"Caitlyn M. Matherne, Jordan E. Wroblewski, Heather S Drago, Gabriela T Marchan, Alexis R Young, Nkechi Kingsley, Craig P. Plaisance, J. Fotie","doi":"10.1055/a-2326-6277","DOIUrl":"https://doi.org/10.1055/a-2326-6277","url":null,"abstract":"Palladium nanoparticles are dispersed and stabilized in organically modified silicate (Pd@MTES), and characterized by a number of spectroscopic techniques, including FTIR, TEM, SEM, and XPS. The catalytic effect of this material toward the hydrosilylation of aldehydes and ketones is explored, and the scope of the reaction investigated, with 26 examples provided. This reaction proceeds under neat conditions via heterogenous catalysis, and a mechanistic pathway supported by DFT calculations is proposed.","PeriodicalId":510101,"journal":{"name":"Synthesis","volume":"36 4","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-05-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140981228","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}
引用次数: 0
Copper Catalyzed Chemoselective Nitro Reduction 铜催化化学选择性硝基还原
Synthesis Pub Date : 2024-05-14 DOI: 10.1055/a-2326-6363
Thi Minh Thi Le, Mingbing Zhong, P. Jubault, T. Poisson
{"title":"Copper Catalyzed Chemoselective Nitro Reduction","authors":"Thi Minh Thi Le, Mingbing Zhong, P. Jubault, T. Poisson","doi":"10.1055/a-2326-6363","DOIUrl":"https://doi.org/10.1055/a-2326-6363","url":null,"abstract":"The reduction of nitro compounds into the highly valuable anilines was reported using a Cu-catalyst and B2Pin2. The reaction proceeded under very mild reaction conditions and showcased an excellent functional group tolerance. This method was applied to a large panel of nitro derivatives including biorelevant molecules and important synthetic intermediates toward the synthesis of API. This novel reaction manifold intends to provide a complementary approach to the existing portfolio of nitro-reduction methods.","PeriodicalId":510101,"journal":{"name":"Synthesis","volume":"21 3","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-05-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140982250","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}
引用次数: 0
Sodium-mediated Reductive anti-Dimagnesiation of Diarylacetylenes with Magnesium Bromide 钠介导的二芳基乙炔与溴化镁的还原反二甲基化反应
Synthesis Pub Date : 2024-05-14 DOI: 10.1055/a-2326-6416
Haruka Yamaguchi, Fumiya Takahashi, Takashi Kurogi, Hideki Yorimitsu
{"title":"Sodium-mediated Reductive anti-Dimagnesiation of Diarylacetylenes with Magnesium Bromide","authors":"Haruka Yamaguchi, Fumiya Takahashi, Takashi Kurogi, Hideki Yorimitsu","doi":"10.1055/a-2326-6416","DOIUrl":"https://doi.org/10.1055/a-2326-6416","url":null,"abstract":"Diarylacetylenes undergo anti-dimagnesiation using magnesium bromide and Na dispersion to afford (E)-1,2-dimagnesioalkenes. This dimagnesiation utilizes simple MgBr2 as a reduction-resistant electrophile, contrasting with the previously reported dimagnesiation using tricky organomagnesium halides. The resulting vicinal double Grignard reagents react with various electrophiles to yield multi-substituted alkenes stereoselectively.","PeriodicalId":510101,"journal":{"name":"Synthesis","volume":"79 23","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-05-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140979013","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}
引用次数: 0
BF3·OEt2 Mediated (3+2) Cycloaddition Reactions of DACs with Cyanamides: Access to Cyclic Amidines BF3-OEt2 介导的 DAC 与氰酰胺的 (3+2) 环加成反应：获得环酰胺
Synthesis Pub Date : 2024-05-13 DOI: 10.1055/a-2323-0721
B. Gopal, Prasoon Raj Singh, Shubham Bhatt, Avijit Goswami
{"title":"BF3·OEt2 Mediated (3+2) Cycloaddition Reactions of DACs with Cyanamides: Access to Cyclic Amidines","authors":"B. Gopal, Prasoon Raj Singh, Shubham Bhatt, Avijit Goswami","doi":"10.1055/a-2323-0721","DOIUrl":"https://doi.org/10.1055/a-2323-0721","url":null,"abstract":"A BF3·OEt2 promoted facile synthesis of cyclic amidines has been developed via the (3+2)-cycloaddition of cyanamides with donor-acceptor cyclopropanes (DACs). In addition to this, the protocol has been successfully extended to construct dimerized amidine derivative and gram-scale synthesis with great efficiency.","PeriodicalId":510101,"journal":{"name":"Synthesis","volume":"122 45","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-05-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140985334","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}
引用次数: 0
SYNFORM ISSUE 2024/6 同步信息》第 2024/6 期
Synthesis Pub Date : 2024-05-13 DOI: 10.1055/s-0040-1763986
M. Zanda
{"title":"SYNFORM ISSUE 2024/6","authors":"M. Zanda","doi":"10.1055/s-0040-1763986","DOIUrl":"https://doi.org/10.1055/s-0040-1763986","url":null,"abstract":"","PeriodicalId":510101,"journal":{"name":"Synthesis","volume":"119 34","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-05-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140985493","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}
引用次数: 0
Remote-Carbonyl-Directed Consecutive Arylation of Terminal Alkenes for the Synthesis of Tetrasubstituted Olefins 末端烯烃的远程羰基定向连续芳基化以合成四代烯烃
Synthesis Pub Date : 2024-05-10 DOI: 10.1055/a-2323-0633
Kun Li, Runze Luan, Yu Du, Weiping Su
{"title":"Remote-Carbonyl-Directed Consecutive Arylation of Terminal Alkenes for the Synthesis of Tetrasubstituted Olefins","authors":"Kun Li, Runze Luan, Yu Du, Weiping Su","doi":"10.1055/a-2323-0633","DOIUrl":"https://doi.org/10.1055/a-2323-0633","url":null,"abstract":"The highly efficient synthesis of all-carbon tetrasubstituted olefins has been concerned for decades, especially for multi-aryl substituted olefins which widely used in functional organic materials and pharmaceuticals. This work presents a carbonyl-directed palladium-catalyzed consecutive arylation of terminal alkenes with aryl iodides under mild conditions, a series of triarylated tetrasubstituted olefins were obtained in moderate yields. Because a weak chelation effect is generally difficult to support such a thorough tri-fold Heck arylation, and the β-trans-selective alkenyl C–H activation cannot be achieved via a twisted endo-metallacyclic intermediate, thus, the key to success is the compatibility between several mechanisms, including Heck, C–H activation and E,Z-isomerization. Here, the judicious selection of a flexible-alkyl-chain-tethered carbonyl group seems to be critical, it provides a proper chelation effect that not only assists a distal alkenyl functionalization or isomerization, but also avoids byproducts caused by other possible β-H elimination or migration. The strategy developed herein greatly streamlines the preparation of the target molecules, and the protocol covers a range of readily available terminal alkenes bearing native directing groups (e.g., aldehyde, ketone and ester), and aryl iodides.","PeriodicalId":510101,"journal":{"name":"Synthesis","volume":" 27","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-05-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140992704","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}
引用次数: 0
A synthesis of dibenzo[b,h][1,5]naphthyridin-7(12H)-ones: the Pictet–Spengler reaction vs a rearrangement of 4-phenyl[1,3]oxazolo[4,5-c]quinolines 二苯并[b,h][1,5]萘啶-7(12H)-酮的合成：皮克泰-斯彭勒反应与 4-苯基[1,3]恶唑并[4,5-c]喹啉的重排反应
Synthesis Pub Date : 2024-05-10 DOI: 10.1055/a-2323-0770
A. Shatsauskas, Sergey A. Kirnosov, Ekaterina S. Keyn, V. Shuvalov, A. Kostyuchenko, A. Fisyuk
{"title":"A synthesis of dibenzo[b,h][1,5]naphthyridin-7(12H)-ones: the Pictet–Spengler reaction vs a rearrangement of 4-phenyl[1,3]oxazolo[4,5-c]quinolines","authors":"A. Shatsauskas, Sergey A. Kirnosov, Ekaterina S. Keyn, V. Shuvalov, A. Kostyuchenko, A. Fisyuk","doi":"10.1055/a-2323-0770","DOIUrl":"https://doi.org/10.1055/a-2323-0770","url":null,"abstract":"Two approaches were proposed to the synthesis of dibenzo[b,h][1,5]naphthyridin-7(12H)-ones. The one-step method based on the Pictet–Spengler reaction of 3-amino-2-phenylquinolin-4(1H)-one with aromatic aldehydes requires heating in a strong acidic media, which leads to significant limitations on the possible products. The second approach is based on the conversion of 3-amino-2-phenylquinolin-4(1H)-one to 4-phenyl[1,3]oxazolo[4,5-c]quinolines followed by rearrangement under the action of AlCl3. A significant advantage of the two-step synthesis is the possibility of obtaining a wider range of dibenzo[b,h][1,5]naphthyridin-7(12H)-ones, including those not available using the Pictet–Spengler reaction.","PeriodicalId":510101,"journal":{"name":"Synthesis","volume":" 32","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-05-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140993553","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}
引用次数: 0
Comprehensive Strategies on the Synthesis of Ene-Yne Derivatives 合成炔-炔衍生物的综合策略
Synthesis Pub Date : 2024-05-01 DOI: 10.1055/a-2317-7262
Kamal Kant, Chandresh K. Patel, Reetu Reetu, Yaqoob A. Teli, Priyadarshini Naik, Sanjukta Some, C. Hazra, N. Aljaar, Ananta K. Atta, C. Malakar
{"title":"Comprehensive Strategies on the Synthesis of Ene-Yne Derivatives","authors":"Kamal Kant, Chandresh K. Patel, Reetu Reetu, Yaqoob A. Teli, Priyadarshini Naik, Sanjukta Some, C. Hazra, N. Aljaar, Ananta K. Atta, C. Malakar","doi":"10.1055/a-2317-7262","DOIUrl":"https://doi.org/10.1055/a-2317-7262","url":null,"abstract":"The process of crafting 1,3-enyne compounds holds widespread appeal in organic synthesis due to the compound's proven adaptability as an intermediate in many methods for creating compounds of significant biological and material interest. A variety of methods have been designed to formulate 1,3-enynes from diverse initial materials, such as alkynes, 1,3-conjugated diynes, cyclopropane substitutes, and propargyl alcohols. This review encapsulates a thorough synthesis of 1,3-enynes by utilizing distinct procedures: homo- and cross-coupling of alkynes, metal/acid-induced cyclopropane ring opening through a nucleophile assault, propargyl alcohols' rearrangement/dehydration sequence. In both the alkyne and 1,3-diyne procedures, managing the regio-, stereo-, and, where fitting, chemoselectivity is a key concern. In contrast, with the cyclopropyl ring opening procedure, the selection of enynes relies on nucleophile orientation. In this context, we underscore select efficient methods for the broad and selective synthesis of these pivotal compounds. Additionally, we provided specific examples to demonstrate the efficacy of these processes.","PeriodicalId":510101,"journal":{"name":"Synthesis","volume":"73 11","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-05-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141052699","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}
引用次数: 0
Asymmetric Hydrogenative Coupling of Indoles with Unsaturated Ketones Enabled by Copper/Ruthenium Relay Catalysis 铜/钌接力催化吲哚与不饱和酮的不对称氢化偶联反应
Synthesis Pub Date : 2024-03-26 DOI: 10.1055/a-2295-5417
Jian Zhang, Chen Guo, Weijun Tang, Dong Xue, Huaming Sun, Jianliang Xiao, Chao Wang
{"title":"Asymmetric Hydrogenative Coupling of Indoles with Unsaturated Ketones Enabled by Copper/Ruthenium Relay Catalysis","authors":"Jian Zhang, Chen Guo, Weijun Tang, Dong Xue, Huaming Sun, Jianliang Xiao, Chao Wang","doi":"10.1055/a-2295-5417","DOIUrl":"https://doi.org/10.1055/a-2295-5417","url":null,"abstract":"A relay catalytic system has been developed for the asymmetric hydrogenative coupling of indoles with α,β-unsaturated ketones, affording enantioenriched chiral γ-indole alcohols with broad substrate scope and excellent enantioselectivities (32 examples, up to >99% ee). Mechanistic studies suggest that the relay catalytic system consists of a copper-catalyzed alkylation and ruthenium-catalyzed asymmetric hydrogenation.","PeriodicalId":510101,"journal":{"name":"Synthesis","volume":"114 20","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-03-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140380236","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}
引用次数: 0
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