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With Tag: Heterocyclic Compounds

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Trimethylsilyldiazomethane as a Versatile Stitching Agent for the Introduction of Aziridines into Functionalized Organic Molecules

Hong Ren, William D. Wulff
Organic Letters | 2010 | 10.1021/ol102064b

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Carboxylate-Assisted Ruthenium-Catalyzed Alkyne Annulations by C–H/Het–H Bond Functionalizations

Lutz Ackermann
Acc. Chem. Res. | 2013 | 10.1021/ar3002798

To improve the atom- and step-economy of organic syntheses, researchers would like to capitalize upon the chemistry of otherwise inert carbon–hydrogen (C–H) bonds. During the past decade, remarkable progress in organometallic chemistry has set the stage for...

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Asymmetric Hydrogenation of Heteroaromatic Compounds

Yong-Gui Zhou
Acc. Chem. Res. | 2007 | 10.1021/ar700094b

Asymmetric hydrogenation of heteroaromatic compounds has emerged as a promising new route to saturated or partially saturated chiral heterocyclic compounds. In this Account, we outline recent advances in asymmetric hydrogenation of heteroaromatic compounds,...

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Palladium-Catalyzed Highly Regio- and Stereoselective Synthesis of 4-Alkylidene-4H-3,1-benzoxazines from N-Acyl-o-alkynylanilines

Takao Saito, Shohei Ogawa, Naoya Takei, Noriki Kutsumura, Takashi Otani
Organic Letters | 2011 | 10.1021/ol103130s

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A Highly Efficient and Selective Route to Isomeric Cyclic Diazadienes

Mark E. Scott, Yann Bethuel, Mark Lautens
Journal of American Chemical Society | 2007 | 10.1021/ja067304r

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Copper(II)-Catalyzed Enantioselective Intramolecular Carboamination of Alkenes

Wei Zeng, Sherry R. Chemler
Journal of the American Chemical Society | 2007 | 10.1021/ja0762240

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Metathesis and Metallotropy:  A Versatile Combination for the Synthesis of Oligoenynes

Mansuk Kim, Daesung Lee
Journal of American Chemical Society | 2005 | 10.1021/ja057153c

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Catalytic Asymmetric [4 + 2] Cycloadditions of Ketenes and N-Thioacyl Imines:  Alternatives for Direct Mannich Reactions of Enolizable Imines

Xuan Xu, Kan Wang, Scott G. Nelson
Journal of American Chemical Society | 2007 | 10.1021/ja074845n

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Synthesis of Chiral 2-(4-Phenoxyphenylsulfonylmethyl)thiiranes as Selective Gelatinase Inhibitors

Samy O. Meroueh, Stephen Brown, M. Margarida Bernardo, Mijoon Lee, Shahriar Mobashery, Rafael Fridman
Org. Lett. | 2005 | 10.1021/ol0517269

Compound 1, 2-(4-phenoxyphenylsulfonylmethyl)thiirane, is a selective inhibitor of gelatinases, which is showing high promise in studies of animal models for cancer metastasis and stroke. The (R)-1 and (S)-1 enantiomers of compound 1 were each synthesized in...

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Organocatalytic Enantioselective Friedel−Crafts Reaction of Pyrrole Derivatives with Imines

Emily B. Rowland, Guilong Li, Jon C. Antilla, Gerald B. Rowland
Org. Lett. | 2007 | 10.1021/ol701881j

A highly enantioselective Friedel−Crafts reaction of pyrrole derivatives with N-acyl imines catalyzed by chiral phosphoric acids was developed. The reactions produced the pyrrole derivatives in high yields and enantioselectivity.

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Asymmetric Synthesis of the (S)-1,1-Dioxido-isothiazolidin-3-one Phosphotyrosine Mimetic via Reduction of a Homochiral (R)-Oxido-isothiazolidin-3-one

Brian Glass, Mei Li, Andrew P. Combs, Laurine G. Galya
Org. Lett. | 2007 | 10.1021/ol0701262

The first asymmetric synthesis of the (S)-1,1-dioxido-isothiazolidin-3-one ((S)-IZD) pTyr mimetic, which has been incorporated into the recently reported potent protein tyrosine phosphatase 1B (PTP1B) inhibitors, is presented herein. The key reaction is the...

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Iron-Promoted Cyclization/Halogenation of Alkynyl Diethyl Acetals

Zhengkun Yu, Tongyu Xu, Liandi Wang
Org. Lett. | 2009 | 10.1021/ol9005689

FeCl 3 - and FeBr 3 -promoted cyclization/halogenation of alkynyl diethyl acetals has been efficiently realized, selectively affording (E)-2-(1-halobenzylidene or alkylidene)-substituted five-membered carbo- and heterocycles which were then efficiently...

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Stereoselective Synthesis of 4-Hydroxy-2,3,6-trisubstituted Tetrahydropyrans

Rachael A. Hughes, Conor St. J. Barry, Christine L. Willis, Gregory D. Parker, John R. Harding, Stuart R. Crosby, Clare D. King
Org. Lett. | 2003 | 10.1021/ol0346180

Reaction of homoallylic alcohols with aldehydes in the presence of TFA gives, after hydrolysis of the ester, 4-hydroxy-2,3,6-trisubstituted tetrahydropyrans with the creation of three new stereocenters in a single-pot process. By varying the aldehyde...

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Two-Component Approach Toward a Fully Substituted N-Fused Pyrrole Ring

Dmitri Chernyak, Vladimir Gevorgyan, Cathy Skontos
Org. Lett. | 2010 | 10.1021/ol1011949

An efficient two-component palladium-catalyzed arylation/cyclization cascade approach toward a variety of N-fused pyrroloheterocycles has been developed. This transformation proceeds via the palladium-catalyzed coupling of aryl halides with propargylic esters...

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Highly Chemoselective 2,4,5-Triaryl-1,3-dioxolane Formation from Intermolecular 1,3-Dipolar Addition of Carbonyl Ylide with Aryl Aldehydes

Wen-Hao Hu, Chong-Dao Lu, Zhi-Yong Chen, Hui Liu, Ai-Qiao Mi
Org. Lett. | 2004 | 10.1021/ol0489494

Rhodium(II) acetate catalyzed 1,3-dipolar cycloaddition of methyl phenyldiazoacetate with a mixture of electron-rich and electron-deficient aryl aldehydes gave 1,3-dioxolanes in high yield with excellent chemoselectivity.

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A General Method for the Enantioselective Synthesis of α-Chiral Heterocycles

Thien S. Nguyen, Jeremy A. May, Phong Q. Le
Org. Lett. | 2012 | 10.1021/ol3030605

The enantioselective formation of stereocenters proximal to unprotected heterocycles has been accomplished. Thus, vinyl boronic acids are added to heterocycle-appended enones via a modified-BINOL catalyst. Catalyst design was key to enable a general reaction....

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Transmetalation of Z-Telluroenynes: Stereoselective Synthesis of Z-Enynols and Their Application in Palladium-Catalyzed Cyclization

Bibiana M. Gay, Caroline C. Schneider, Gilson Zeni, Helton Caldeira, Davi F. Back
Org. Lett. | 2010 | 10.1021/ol902896x

The synthesis of various Z-enynols via reaction of vinyllithium intermediate with aldehydes and ketones is described. The subsequent cyclization of a wide variety of Z-enynols afforded substituted furans and dihydrofurans with high regioselectivity under mild...

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Trifluoroacetic Anhydride Promoted Tandem Conjugate Addition of Boronic Acids/Acetal Ring Opening

Aurelio G. Csákÿ, Silvia Roscales
Org. Lett. | 2012 | 10.1021/ol300272j

A new stereoselective tandem reaction consisting of the metal-free conjugate addition of boronic acids followed by an intramolecular ring opening of a cyclic acetal has been disclosed. Optically pure polysubstituted tetrahydropyrans have been synthesized...

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Enantioselective Michael Addition/Iminium Ion Cyclization Cascades of Tryptamine-Derived Ureas

David M. Barber, Isabelle Aillaud, Amber L. Thompson, Darren J. Dixon
Org. Lett. | 2013 | 10.1021/ol401039h

A Michael addition/iminium ion cyclization cascade of enones with tryptamine-derived ureas under BINOL phosphoric acid (BPA) catalysis is reported. The cascade reaction tolerates a wide variety of easily synthesized tryptamine-derived ureas, including those...

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Palladium-Catalyzed Carbonylative Cyclization/Arylation Cascade for 2-Aroylindolizine Synthesis

Vladimir Gevorgyan, Dmitri Chernyak, Zhou Li
Org. Lett. | 2012 | 10.1021/ol302947r

An efficient synthesis of densely substituted 2-aroylindolizines via the palladium-catalyzed carbonylative cyclization/arylation is reported. This transformation proceeds via the 5-endo-dig cyclization of 2-propargylpyridine triggered by an aroyl Pd complex....

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