58754-95-3Relevant articles and documents
Iron-Catalyzed Diastereoselective Synthesis of Disubstituted Morpholines via C-O or C-N Bond Formation
Aubineau, Thomas,Dupas, Alexandre,Zeng, Tian,Cossy, Janine
supporting information, p. 525 - 531 (2020/08/28)
The diastereoselective synthesis of 2,6- and 3,5-disubstituted morpholines was achieved from 1,2-amino ethers and 1,2-hydroxy amines substituted by an allylic alcohol using an iron(III) catalyst. The morpholines were obtained either by C-O or C-N bond formation. A plausible mechanism is suggested, involving a thermodynamic equilibrium to explain the formation of the cis diastereoisomer as the major product.
Iron-catalyzed alkyne-carbonyl metathesis for the synthesis of 6,7-dihydro-5H-dibenzo[c,e]azonines
Chakraborty, Baitan,Jana, Umasish
supporting information, p. 10549 - 10553 (2021/12/27)
The synthesis of nine-membered ringsviaalkyne-carbonyl metathesis is reported. The alkyne and acetal units contained in a biaryl substrate undergo the intramolecular alkyne-carbonyl metathesis reaction under FeCl3-catalysis to furnish the unexp
Copper-catalyzed cycloisomerization of unactivated allene-tethered O-propargyl oximes: A domino reaction sequence toward the synthesis of hexahydropyrrolo[3,4- b]azepin-5(4 H)-ones
Nikbakht, Ali,Amiri, Kamran,Khosravi, Hormoz,Zhou, Yirong,Balalaie, Saeed,Breit, Bernhard
supporting information, p. 3343 - 3348 (2021/05/07)
A novel copper-catalyzed cycloisomerization of unactivated allene-tethered O-propargyl oximes has been developed for the synthesis of hexahydropyrrolo[3,4-b]azepin-5(4H)-ones. This one-pot domino reaction proceeds via a [2,3]-sigmatropic rearrangement, a
Palladium-Catalyzed C(sp3)?H Arylation of Primary Amines Using a Catalytic Alkyl Acetal to Form a Transient Directing Group
St John-Campbell, Sahra,Ou, Alex K.,Bull, James A.
supporting information, p. 17838 - 17843 (2018/11/23)
C?H Functionalization of amines is a prominent challenge due to the strong complexation of amines to transition metal catalysts, and therefore typically requires derivatization at nitrogen with a directing group. Transient directing groups (TDGs) permit C?H functionalization in a single operation, without needing these additional steps for directing group installation and removal. Here we report a palladium catalyzed γ-C?H arylation of amines using catalytic amounts of alkyl acetals as transient activators (e.g. commercially available (2,2-dimethoxyethoxy)benzene). This simple additive enables arylation of amines with a wide range of aryl iodides. Key structural features of the novel TDG are examined, demonstrating an important role for the masked carbonyl and ether functionalities. Detailed kinetic (RPKA) and mechanistic investigations determine the order in all reagents, and identify cyclopalladation as the turnover limiting step. Finally, the discovery of an unprecedented off-cycle free-amine directed ?-cyclopalladation of the arylation product is reported.
Synthesis of Indole-Dihydroisoquinoline Sulfonyl Ureas via Three-Component Reactions
Pearson, Stuart E.,Fillery, Shaun M.,Goldberg, Kristin,Demeritt, Julie E.,Eden, Jonathan,Finlayson, Jonathan,Patel, Anil
, p. 4963 - 4981 (2018/12/13)
Isoquinolines activated with sulfamoyl chlorides were reacted with indoles in a 3-component reaction to generate a library of dihydroisoquinoline derivatives. Using a differential protecting group strategy, products could be further derivatised. Synthesis of isoquinoline starting materials using several different methods is also described.
α-Amino Aldehydes as Readily Available Chiral Aldehydes for Rh-Catalyzed Alkyne Hydroacylation
Hooper, Joel F.,Seo, Sangwon,Truscott, Fiona R.,Neuhaus, James D.,Willis, Michael C.
supporting information, p. 1630 - 1634 (2016/02/20)
Readily available α-amino aldehydes, incorporating a methylthiomethyl (MTM) protecting group on nitrogen, are shown to be efficient substrates in Rh-catalyzed alkyne hydroacylation reactions. The reactions are performed under mild conditions, employing a small-bite-angle bis-phosphine ligand, allowing for good functional group tolerance with high stereospecificity. Amino aldehydes derived from glycine, alanine, valine, leucine, phenylalanine, isoleucine, serine, tryptophan, methionine, and cysteine were successfully employed, as was an enantiomerically enriched α-OMTM-aldehyde derived from phenyllactic acid. The synthetic utility of the α-amino enone products is demonstrated in a short enantioselective synthesis of the natural product sphingosine.
Gold-Catalyzed Fluorination–Hydration: Synthesis of α-Fluorobenzofuranones from 2-Alkynylphenol Derivatives
Wang, Qiang,Jiang, Yu,Sun, Run,Tang, Xiang-Ying,Shi, Min
supporting information, p. 14739 - 14745 (2016/10/03)
The AuI-catalyzed fluorination–hydration of 2-alkynylphenol derivatives in the presence of Selectfluor [1-chloromethyl-4-fluoro-1,4-diazoniabicyclo-[2.2.2]octane bis(tetrafluoroborate)] has been developed. This method provides straightforward a
Access to Polyfunctionalized Chiral Piperidines through Enantioselective Addition-Carbocyclization Cascade Reaction Catalyzed by a Rhodium(I)-Diene Complex
Serpier, Fabien,Brayer, Jean-Louis,Folléas, Beno?t,Darses, Sylvain
supporting information, p. 5496 - 5499 (2015/11/18)
A new addition-carbocyclization cascade reaction initiated by arylboronic acids and catalyzed by a rhodium/chiral diene complex is described. Starting from N-bridged oxoenoate derivatives, highly functionalized piperidines bearing three contiguous stereogenic centers were obtained with excellent enantio- and diastereoselectivities.
Vinyl dihydropyrans and dihydrooxazines: Cyclizations of catalytic ruthenium carbenes derived from alkynals and alkynones
Cambeiro, Fermin,Lopez, Susana,Varela, Jesus A.,Saa, Carlos
supporting information, p. 5959 - 5963 (2014/06/10)
A novel synthesis of 2-vinyldihydropyrans and dihydro-1,4-oxazines (morpholine derivatives) from alkynals and alkynones has been developed. The cyclizations require a mild generation of catalytic ruthenium carbenes from terminal alkynes and (trimethylsilyl)diazomethane followed by trapping with carbonyl nucleophiles. Mechanistic aspects of the new cyclizations are discussed. Setting a trap: A novel synthesis of 2-vinyldihydropyrans and dihydro-1,4-oxazines (morpholine derivatives) from alkynals and alkynones has been developed. The cyclizations require a mild generation of catalytic ruthenium carbenes from terminal alkynes and (trimethylsilyl)diazomethane followed by trapping with carbonyl nucleophiles.
Gold-catalyzed intramolecular regio- and enantioselective cycloisomerization of 1,1-bis(indolyl)-5-alkynes
Huang, Long,Yang, Hai-Bin,Zhang, Di-Han,Zhang, Zhen,Tang, Xiang-Ying,Xu, Qin,Shi, Min
supporting information, p. 6767 - 6771 (2013/07/25)
Bis(indole) alkaloids analogues were prepared under mild conditions and in high yields through a gold-catalyzed cycloisomerization of 1,1-bis(indolyl)-5- alkynes (see scheme). The enan Copyright