- Regioselective addition of pyrrole to N-tosyl imines in the presence of Cu(OTf)2
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The Cu(OTf)2 catalysed reaction of pyrrole with N-tosyl imines gives pyrrole sulfonamides in high yields. The addition reaction takes place regioselectively at C(2) of the pyrrole. The procedure is simple and does not require anhydrous conditio
- Temelli, Baris,Unaleroglu, Canan
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Read Online
- NHC ligand-enabled Ni-catalyzed reductive coupling of alkynes and imines using isopropanol as a reductant
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A nickel-catalyzed reductive coupling of alkynes and imines using readily available isopropanol as the reducing agent was developed. The use of a sterically bulky and electron-rich carbene ligand (AnIPr) significantly promotes the reaction, providing various multi-substituted allylic amines in 23-89% yield and the corresponding chiral ligand (AnIPr-3) can afford the products in 51-95% ee.
- Yao, Wei-Wei,Li, Ran,Li, Jiang-Fei,Sun, Juan,Ye, Mengchun
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Read Online
- The diastereoselective synthesis of 2,3-diaryl-3-cyano-substituted pyrrolidines via the MgI2 mediated ring expansion of aryl cyclopropyl nitriles
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The MgI2 mediated reaction of aryl substituted cyclopropyl nitriles with tosyl aldimines to give 2,3-diaryl-3-cyano-substituted pyrrolidines has been demonstrated. In all cases, the trans-diastereoisomer was determined to be the major product.
- Stead, Darren
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supporting information
(2020/09/04)
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- Iron-based nanomaterials used as magnetic mesoporous nanocomposites to catalyze the preparation of N-sulfonylimines
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A new magnetic nanocatalyzed synthetic method for the synthesis of aldimines was evidenced. The reaction was carried out in a Schlenk tube under reflux conditions using various solvents and different nanomaterials as catalysts. In these reactions, an exce
- Ashouri, Akram,Samadi, Saadi,Nasiri, Behzad,Bahrami, Zohre
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p. 549 - 556
(2019/08/01)
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- Synthesis of novel N-(p-toluenesulfonyl)aminophosphonates and evaluation of their biological properties
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The synthesis of a series of N-sulfonylaminophosphonates 2aA-2dC and evaluation of their cytotoxicity and ecotoxicity is described. N-sulfonylaminophsophonates 2aA-2dC were obtained by addition of dialkyl phosphites to azomethine bonds of sulfonimines 1a-
- Karpowicz, Rafa?,Lewkowski, Jaros?aw,Stasiak, Ma?gorzata,Czopor, Aleksandra,Tokarz, Paulina,Król, Adrianna,Rogacz, Diana,Rychter, Piotr
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p. 423 - 436
(2018/02/06)
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- Visible-light, iodine-promoted formation of n-sulfonyl imines and n-alkylsulfonamides from aldehydes and hypervalent iodine reagents
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Alternative synthetic methodology for the direct installation of sulfonamide functionality is a highly desirable goal within the domain of drug discovery and development. The formation of synthetically valuable N-sulfonyl imines from a range of aldehydes,
- Hopkins, Megan D,Brandeburg, Zachary C.,Hanson, Andrew J.,Lamar, Angus A
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- A Gold Carbene Manifold to Prepare Fused γ-Lactams by Oxidative Cyclisation of Ynamides
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Gold-catalysed oxidative cyclisation reactions of ynamides offer great promise in γ-lactam synthesis but are limited by preferential over-oxidation to form α-keto imides. Evaluating the factors that might limit N-cyclisation pathways led to effective gold-catalysed conditions that allow access to different fused γ-lactams on changing the ynamide N-substituent and accommodate previously incompatible substitution patterns. New and efficient methods for the synthesis of functionalised 3-aryl indoles and cyclohepta[c]pyrrol-1-one derivatives are presented. These conditions illustrate the complementarity of gold catalysis to other metals.
- Sánchez-Cantalejo, Fernando,Priest, Joshua D.,Davies, Paul W.
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supporting information
p. 17215 - 17219
(2018/11/10)
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- Visible-Light-Mediated Decarboxylative Benzylation of Imines with Arylacetic Acids
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A straightforward method for the visible-light-mediated decarboxylative benzylation of imines is reported. The key feature of this method is the use of simple primary, secondary, and tertiary arylacetic acids as precursors of benzyl radicals, enabling the facile benzylation of a variety of imines under mild conditions. A variety of structurally diverse β-arylethylamines (37 examples) was accessed using this method.
- Guo, Jing,Wu, Qiao-Lei,Xie, Ying,Weng, Jiang,Lu, Gui
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p. 12559 - 12567
(2018/10/20)
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- Formation of: N -sulfonyl imines from iminoiodinanes by iodine-promoted, N-centered radical sulfonamidation of aldehydes
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A mild and operationally convenient formation of synthetically valuable N-sulfonyl imines from a range of aryl aldehydes by reaction with iminoiodinanes (PhINZ) and I2 has been developed. According to mechanistic experiments described within, the reaction is speculated to proceed through an unconventional light-promoted, N-centered radical (NCR) pathway involving a N,N-diiodosulfonamide reactive species. This method not only provides a new pathway toward the production of activated imines, but also serves as an example of a non-traditional means of carbonyl activation via an NCR species.
- Hopkins, Megan D.,Scott, Kristina A.,Demier, Brettany C.,Morgan, Heather R.,Macgruder, Jesse A.,Lamar, Angus A.
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p. 9209 - 9216
(2017/11/14)
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- Tunable titanocene lewis acid catalysts for selective friedel-crafts reaction of indoles and N-sulfonylaldimines
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A newc strategy to control the selective Friedel-Crafts reaction of indoles and imines under mild conditions was developed. Phenol derivatives were established as efficient ligands to finely tune the activity of titanocene dichloride. Cp2TiCl2 and phenol catalyzed the mono-Friedel-Crafts reaction of indoles and N-sulfonyl aldimines with good yields (91 %), whereas o-aminophenol significantly enhanced the activity of the titanocene catalyst and promoted the synthesis of bisindole with excellent yields (98 %). The new organometallic Lewis acid catalysts are air-tolerant, can be used with low catalyst loading (3 mmol-%) and are compatible with -NO2, -F, -Cl, -Br, and -OMe (30 examples with yields from good to excellent). The titanocene catalysts were fully characterized by NMR and HRMS analysis. The results suggest that Cp2TiCl(OC6H5) (I) and Cp2TiCl(OC6H4NH3+Cl-) (II) were catalytic species for the mono- and double-Friedel-Crafts reactions, respectively. Distinguished from single functional acid catalysts I, catalyst II showed a catalytic cooperative effect of two acid components, which led to a fine tuning of the reactivity as well as to the selectivity of the desired reaction pathways. A Ti-catalyzed, highly selective Friedel-Crafts reaction of indoles and imines has been developed. Cp2TiCl2 and phenol, with a single Lewis acid site, catalyzed the mono-Friedel-Crafts reaction of indoles and N-sulfonylaldimines, whereas o-aminophenol enhanced the acidity of titancene catalyst, enabling both Lewis and Bronsted acid sites to promote the synthesis of bisindole.
- Xiu, Wang,Zhenhua, Wang,Zhang, Guofang,Zhang, Weiqiang,Wu, Ya,Gao, Ziwei
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supporting information
p. 502 - 507
(2016/02/18)
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- Assembly of homoallylamine derivatives through iron-catalyzed three-component sulfonamidoallylation reaction
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An efficient FeCl3-catalyzed three-component reaction between aldehydes, sulfonamides and allylsilanes has been achieved, which provides a convenient, atom-economic and green way to construct homoallylamine derivatives. In addition, this reaction exhibits excellent syn stereoselectivity with γ-substituted allylsilanes. A practical three-component cascade process to homoallylamine derivatives is reported, which uses cheap and environmentally benign FeCl3 as catalyst and shows excellent syn stereoselectivity with γ-substituted allylsilanes.
- Fan, Xiaohui,Zhu, Hong-Bo,Lv, Hao,Guo, Kun,Guan, Yong-Hong,Cui, Xiao-Meng,An, Bin,Pu, Yan-Ling
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p. 588 - 592
(2015/09/01)
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- Silver(I)-catalyzed route to pyrroles: Synthesis of halogenated pseudilins as allosteric inhibitors for myosin atpase and x-ray crystal structures of the protein-inhibitor complexes
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The pentahalogenated 2-arylpyrrole-type alkaloids pentabromopseudilin and pentachloropseudilin represent a new class of isoform-specific allosteric inhibitors of myosin ATPase. Herein, we describe an application of the silver(I)-catalyzed cycloisomerizati
- Martin, Rene,Risacher, Celia,Barthel, Andre,Jaeger, Anne,Schmidt, Arndt W.,Richter, Sabine,Boehl, Markus,Preller, Matthias,Chinthalapudi, Krishna,Manstein, Dietmar J.,Gutzeit, Herwig O.,Knoelker, Hans-Joachim
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p. 4487 - 4505
(2014/08/05)
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- A general aminocatalytic method for the synthesis of aldimines
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A general and efficient biomimetic method for the synthesis of aldimines from aldehydes and compounds bearing the NH2 group in the presence of pyrrolidine as a catalyst has been developed. These organocatalytic reactions, based on the application of the concept of nucleophilic catalysis, proceed with outstanding yields in the absence of acids and metals under simple conditions and minimum experimental manipulation. The method has been mainly applied to the synthesis of N-sulfinyl and N-sulfonyl imines, but its general validity has been proven with the preparation of representative N-phosphinoyl, N-alkyl, and N-aryl imines. These unprecedented reactions, which presumably occur via iminium activation without requiring acidic conditions, are an interesting and competitive alternative to the classical methods for preparing aldimines.
- Morales, Sara,Guijarro, Fernando G.,Garcia Ruano, Jose Luis,Cid, M. Belen
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supporting information
p. 1082 - 1089
(2014/02/14)
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- A Mannich/cyclization cascade process for the asymmetric synthesis of spirocyclic thioimidazolidineoxindoles
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An asymmetric cascade Mannich/cyclization reaction between 3-isothiocyanato oxindoles and sulfimides using a commercially available organocatalyst has been developed. A wide range of structurally diverse spiro[imidazolidine-4,3′-oxindole] derivatives were
- Cai, Hao,Zhou, Yu,Zhang, Dong,Xu, Jinyi,Liu, Hong
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supporting information
p. 14771 - 14774
(2015/01/09)
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- Diastereoselective synthesis of pyrrolidine derivatives via a one-pot nitro-Mannich/hydroamination cascade using base and gold catalysis
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An efficient one-pot nitro-Mannich/hydroamination cascade reaction for the synthesis of substituted pyrrolidines bearing three stereocentres is reported. Proceeding under the control of a combination of base and gold(i) catalysts, the cascade reaction aff
- ?uri?, Andrej,Barber, David M.,Sanganee, Hitesh J.,Dixon, Darren J.
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supporting information
p. 2777 - 2779
(2013/04/23)
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- Nucleophilic addition of regioselectively lithiated indoline with aldimines for the syntheses of 2- and 7-indolinyl methanamine derivatives
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Indolines bearing different N-protecting groups (N-Tbf and N-Boc) were deprotonated regioselectively at C-2 (sp3 hybridized ortho-H) and C-7 (sp2 hybridized para-H) of the indoline ring, respectively. The generated organolithium intermediates reacted with aldimines to give the desired products in good yields with excellent anti-diastereoselectivities (>99:1). The produced N-Ts-(1-Tbf-indolin-2-yl)methanamine was facilely transformed to a fused heterocyclic compound.
- Cheng, Liang,Liu, Li,Li, Chuan,Jia, Han,Wang, Dong,Chen, Yong-Jun
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supporting information; experimental part
p. 4004 - 4007
(2012/09/05)
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- α-Aryl-substituted allenamides in an imino-nazarov cyclization cascade catalyzed by Au(I)
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An imino-Nazarov cyclization using α-aryl-substituted allenamides is described. This gold(I)-catalyzed cascade is efficient and regioselective in constructing a diverse array of synthetically useful aromatic-ring fused cyclopentenamides. The success in this transformation represents a solution to the challenge in establishing an imino-Nazarov cyclization process.
- Ma, Zhi-Xiong,He, Shuzhong,Song, Wangze,Hsung, Richard P.
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supporting information
p. 5736 - 5739
(2013/01/15)
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- Asymmetric addition of diethylzinc to aldehydes catalyzed by new zinc-amides prepared by a rhodium-catalyzed asymmetric addition
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A new chiral zinc-amide 2s' was found to be an effective catalyst for the asymmetric addition of diethylzinc to aldehydes 3 through a screening method for asymmetric catalysts, in which two catalytic asymmetric reactions are connected. The chiral zinc cat
- Yoshida, Kazuhiro,Akashi, Naohisa,Yanagisawa, Akira
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experimental part
p. 1225 - 1230
(2011/10/19)
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- Dinuclear zinc catalyzed asymmetric Friedel-Crafts amidoalkylation of indoles with aryl aldimines
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The asymmetric Friedel-Crafts amidoalkylation of indoles with aryl aldimines could be efficiently catalyzed by Trost's bis-ProPhenol dinuclear zinc complexes to attain 3-indolyl methanamine derivatives in good to excellent yields (85-98%) with moderate to high enantiomeric ratios (from 70:30 up to 95:5 er). Remarkably, this approach provides efficient access to enantiomerically enriched 3-indolyl methanamines, which avoids the formation of the undesirable bis- and tris(indolyl)methanes (BIMs and TIMs) byproduct.
- Wang, Bei-Lei,Li, Nai-Kai,Zhang, Jin-Xin,Liu, Guo-Gui,Liu, Teng,Shen, Qi,Wang, Xing-Wang
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supporting information; experimental part
p. 2614 - 2617
(2011/05/08)
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- One-pot nitro-Mannich/hydroamination cascades for the direct synthesis of 2,5-disubstituted pyrroles using base and gold catalysis
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An efficient, easy to perform, one-pot reaction cascade for the synthesis of 2,5-disubstituted pyrroles from p-toluenesulfonyl protected imines and 4-nitrobut-1-yne under a combination of base and gold(iii) catalysis is reported.
- Barber, David M.,Sanganee, Hitesh,Dixon, Darren J.
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supporting information; body text
p. 4379 - 4381
(2011/06/17)
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- Organic hydrogen phosphites and hydrogen phosphates catalyzed Friedel-Crafts amidoalkylation of indoles with aryl aldimines
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A highly efficient and selective Friedel-Crafts amidoalkylation reaction of indoles with N-Ts aryl aldimines has been developed utilizing dimethyl hydrogen phosphite or diphenyl hydrogen phosphate as the organocatalysts, providing a facile and cost-effect
- Wang, Bei-Lei,Zhang, Jin-Xin,Li, Nai-Kai,Liu, Guo-Gui,Shen, Qi,Wang, Xing-Wang
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supporting information; experimental part
p. 4671 - 4674
(2011/10/01)
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- Asymmetric aza-friedel-crafts reaction of 2-naphthol with tosylimines catalyzed by a dinuclear zinc complex
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The first asymmetric aza-Friedel-Crafts reaction of 2-naphthol with tosylimines was developed via a dinuclear zinc catalyst (up to 98% ee). It provided a new method for the asymmetric synthesis of Betti base derivatives.
- Niu, Liang-Feng,Xin, Yang-Chun,Wang, Ren-Lin,Jiang, Fan,Xu, Peng-Fei,Hui, Xin-Ping
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supporting information; experimental part
p. 765 - 768
(2010/06/14)
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- Total synthesis of pentabromo- and pentachloropseudilin, and synthetic analogues-allosteric inhibitors of myosin ATPase
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Stopping myo: The total syntheses of the title compounds have been achieved using a highly efficient silver(I)- catalyzed cyclization of N-tosyl-homopropargylamines. The pseudilin derivatives represent a novel class of myosin inhibitors. A new allosteric
- Martin, Rene,Jaeger, Anne,Bohl, Markus,Richter, Sabine,Fedorov, Roman,Manstein, Dietmar J.,Gutzeit, Herwig O.,Knolker, Hans-Joachim
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scheme or table
p. 8042 - 8046
(2010/01/16)
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- Synthesis of meso-tetraphenyl porphyrins via condensation of dipyrromethanes with N-tosyl imines
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A new synthetic route for the synthesis of 5,10,15,20-tetraphenyl porphyrins has been developed based on the reaction of 5-substituted dipyrromethanes with N-tosyl imines in the presence of a metal triflate catalyst. meso-Substituted tetraphenyl porphyrins were synthesized in a two-step process. The first step of the method is the metal triflate-catalyzed condensation of 5-substituted dipyrromethanes with N-tosyl imines to form a porphyrinogen intermediate and the second step is the oxidation of the porphyrinogen to porphyrin. The method was applied to the synthesis of trans-A2B2-tetraarylporphyrins and the products were obtained with only a trace amount of one scrambling product. The synthesis of two important building blocks for porphyrin synthesis, mono and di-sulfonamide alkylated 5-substituted dipyrromethanes, was achieved by the addition of 5-substituted dipyrromethane to N-tosyl imine. The application of mono and di-sulfonamide alkylated 5-substituted dipyrromethanes in '2+2' porphyrin formation reactions is presented.
- Temelli, Baris,Unaleroglu, Canan
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experimental part
p. 2043 - 2050
(2009/07/18)
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- Enantioselective organocatalytic anti-Mannich-type reaction of N-unprotected 3-substituted 2-oxindoles with aromatic N-Ts-aldimines
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(Chemical Equation Presented) The modified cinchona alkaloid-catalyzed direct Mannich-type reaction of N-unprotected 2-oxindoles with N-Ts-imine was developed to afford anti-3,3-disubstituted 2-oxindoles with vicinal chiral quaternary and tertiary carbon
- Cheng, Liang,Liu, Li,Jia, Han,Wang, Dong,Chen, Yong-Jun
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supporting information; experimental part
p. 4650 - 4653
(2009/09/25)
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- Base and copper(i) catalyzed Mannich, alkyne hydroamination cascades for the direct synthesis of 2-methylenepyrrolidines
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An efficient, simple-to-perform, one-pot reaction cascade to 2-methylenepyrrolidines from p-toluenesulfonyl protected imines and propargylated malonates under a combination of base and copper(i) catalysis is reported.
- Wang, Hai-Fei,Yang, Ting,Xu, Peng-Fei,Dixon, Darren J.
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supporting information; experimental part
p. 3916 - 3918
(2010/01/06)
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- ORGANIC TELLURIDE-MEDIATED REACTION OF TOSYL AZIDE WITH CARBONYL COMPOUNDS
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Organic telluride induces the reaction of tosyl azide with aldehydes to afford the corresponding N-tosylimines in various yields.Tellurilimine has been suggested as a probable intermediate.
- Suzuki, Hitomi,Takeda, Syoko,Hanazaki, Yasuaki
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p. 679 - 680
(2007/10/02)
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