Papers

With Tag: General Organic Chemistry

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A Ru-Catalyzed Four-Component Coupling

Anthony B. Pinkerton, Barry M. Trost
J. Am. Chem. Soc. | 2000 | 10.1021/ja001656v

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A Ruthenium-Catalyzed Two-Component Addition To Form 1,3-Dienes

Anthony B. Pinkerton, Barry M. Trost
J. Am. Chem. Soc. | 1999 | 10.1021/ja990291f

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Electrophilic α-Amination Reaction of β-Ketoesters Using N-Hydroxycarbamates: Merging Aerobic Oxidation and Lewis Acid Catalysis

Alejandro Bugarin, Javier Read De Alaniz, David Sandoval, Charles P. Frazier
J. Am. Chem. Soc. | 2012 | 10.1021/ja310784f

The copper-catalyzed α-amination of carbonyl compounds using nitrosoformate intermediates as the electrophilic source of nitrogen is reported. The reaction merges aerobic oxidation and Lewis acid catalysis. The scope of the reaction is broad in terms of both...

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Chemoselective Reductions of Nitroaromatics in Water at Room Temperature

Sean M. Kelly, Bruce H. Lipshutz
Org. Lett. | 2013 | 10.1021/ol403079x

A robust and green protocol for the reduction of functionalized nitroarenes to the corresponding primary amines has been developed. It relies on inexpensive zinc dust in water containing nanomicelles derived from the commercially available designer surfactant...

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4,5,6,7-Tetrachlorobenzo[d][1,3,2]dioxaborol- 2-ol as an Effective Catalyst for the Amide Condensation of Sterically Demanding Carboxylic Acids

Hisashi Yamamoto, Toshikatsu Maki, Kazuaki Ishihara
Org. Lett. | 2006 | 10.1021/ol060216r

4,5,6,7-Tetrachlorobenzo[d][1,3,2]dioxaborole (4a) and 4,5,6,7-tetrachlorobenzo[d][1,3,2]dioxaborol-2-ol (4b) are effective catalysts for the dehydrative amide condensation between an equimolar mixture of carboxylic acids and amines. In particular, these...

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CamTHP*OH:  A Camphor-Derived δ-Lactol Auxiliary for the Effective Desymmetrization of Attached Glycinamide Residues. Asymmetric Synthesis of α-Amino Carbonyl Compounds

Nathaniel J. T. Monck, Richard A. J. Horan, Darren J. Dixon
Org. Lett. | 2004 | 10.1021/ol048569i

Stereoselective allylation of camphor and subsequent terminal hydroformylation affords a new δ-lactol auxiliary (camTHP*OH) on multigram scale. Stereoselective condensation with glycine dimethylamide and Cbz protection affords a camTHP*-desymmetrized...

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Amides in One Pot from Carboxylic Acids and Amines via Sulfinylamides

Pierre Vogel, Jianfei Bai, Bartosz K. Zambroń
Org. Lett. | 2014 | 10.1021/ol403508j

An efficient method has been developed for the direct amidification of carboxylic acids via sulfinylamides preformed in situ by the reaction of pure amines with prop-2-ene-1-sulfinyl chloride. The method can be applied to aliphatic acids, including pivalic...

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Reduction of Aldehydes and Ketones by Transfer Hydrogenation with 1,4-Butanediol

Hannah C. Maytum, Bahareh Tavassoli, Jonathan M. J. Williams
Org. Lett. | 2007 | 10.1021/ol702029n

1,4-Butanediol has been used as the hydrogen donor in transfer hydrogenation reactions. The equilibrium is driven by the formation of γ-butyrolactone, and the diol is therefore not required in excess.

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InCl3/Me3SiBr-Catalyzed Direct Coupling between Silyl Ethers and Enol Acetates

Yoshihiro Nishimoto, Yoshiharu Onishi, Makoto Yasuda, Akio Baba
Org. Lett. | 2011 | 10.1021/ol200875m

A combined Lewis acid catalyst of InCl 3 and Me 3 SiBr promoted the direct use of enol acetates in the coupling with low-reactive silyl ethers, in which functional groups including ketones and aldehydes survived. Sterically hindered silyl ethers such as...

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Unusual Highly Regioselective Direct Aldol Additions with a Moisture-Resistant and Highly Efficient Titanium Catalyst

Rainer Mahrwald, Bernd Schetter
Org. Lett. | 2005 | 10.1021/ol052637z

The extremely robust and water-stable tetranuclear complex Ti 4 (μ-BINOLato) 6 3 -OH) 4 was found to catalyze the direct aldol addition with high regioselectivities at the more steric α-encumbered side of unsymmetrical ketones. As few as 0.2 mol %...

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Novel Approach for Asymmetric Synthesis of Fluorinated β-Amino Sulfones and Allylic Amines

Santos Fustero, Ana Bartolomé, Juan García Soler, María Sánchez Roselló
Org. Lett. | 2003 | 10.1021/ol034892u

Enantiomerically pure γ-fluoroalkyl β-amino sulfones are readily synthesized in three steps starting from fluorinated imidoyl chlorides and arylmethyl sulfones. A complementary two-step sequence starting from chiral fluorinated β-amino sulfoxides has also...

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Copper-Catalyzed Nondecarboxylative Cross Coupling of Alkenyltrifluoroborate Salts with Carboxylic Acids or Carboxylates: Synthesis of Enol Esters

Tan D. Quach, Robert A. Batey, Fang Huang
Org. Lett. | 2013 | 10.1021/ol4013712

A mild copper-catalyzed Chan–Lam–Evans type cross-coupling reaction for the regioselective and stereospecific preparation of (E)- or (Z)-enol esters is described. The method couples carboxylate salts or carboxylic acids with potassium alkenyltrifluoroborate...

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Efficient Addition Reaction of Bromonitromethane to Aldehydes Catalyzed by NaI:  A New Route to 1-Bromo-1-nitroalkan-2-ols under Very Mild Conditions

José M. Concellón, Carmen Concellón, Santiago García-Granda, M. Rosario Díaz, Humberto Rodríguez-Solla
Org. Lett. | 2006 | 10.1021/ol062451f

A catalytic NaI-mediated novel synthesis of 1-bromo-1-nitroalkan-2-ols was carried out by reaction of bromonitromethane with a variety of aldehydes, under very mild conditions. When the reaction was performed with chiral N,N-dibenzyl alaninal, the...

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Copper + Nickel-in-Charcoal (Cu−Ni/C): A Bimetallic, Heterogeneous Catalyst for Cross-Couplings

Žarko V. Bošković, Bruce H. Lipshutz, Benjamin R. Taft, Danielle M. Nihan, Ekaterina Vinogradova
Org. Lett. | 2008 | 10.1021/ol801676u

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Chiral Phosphoric Acid-Catalyzed Desymmetrization of meso-Aziridines with Functionalized Mercaptans

Juan C. Baso, Jon C. Antilla, Guilong Li, Shawn E. Larson
Org. Lett. | 2009 | 10.1021/ol902123h

Conditions for the phosphoric acid-catalyzed highly enantioselective ring-opening of meso-aziridines with a series of functionalized aromatic thiol nucleophiles are described. The procedure utilizes commercially available aromatic thiols, a series of...

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New Approach to Oximes through Reduction of Nitro Compounds Enabled by Visible Light Photoredox Catalysis

Shunyou Cai, Yaohong Zhao, David Zhigang Wang, Shaolong Zhang
Org. Lett. | 2013 | 10.1021/ol4009443

A range of nitro compounds are smoothly reduced to their corresponding oximes under the synergistic effects of visible light irradiation, the Ru(bpy) 3 Cl 2 photocatalyst, Hünig’s base, Mg(ClO 4 ) 2 activation, and MeCN solvent. This remarkably mild and...

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Copper-Catalyzed Coupling of Amides and Carbamates with Vinyl Halides

Artis Klapars, Stephen L. Buchwald, Gabriel E. Job, Lei Jiang
Org. Lett. | 2003 | 10.1021/ol035355c

A general and efficient copper-catalyzed method for the amidation of vinyl bromides and iodides has been developed. This protocol uses a combination of 5 mol % copper iodide and 20 mol % N,N‘-dimethyl ethylenediamine. Substrates bearing ester, silyl ether,...

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Expanding the Scope of Trialkylborane/Water-Mediated Radical Reactions

Matthew R. Medeiros, Laura N. Schacherer, John L. Wood, David A. Spiegel
Org. Lett. | 2007 | 10.1021/ol7016609

The dehalogenation of alkyl iodides, as well as the chemoselective deoxygenation of a secondary alcohol in the presence of various alkyl and aryl halides, can be accomplished employing a trialkylborane/air/water system.

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3-Pyrrolidinecarboxylic Acid for Direct Catalytic Asymmetric anti-Mannich-Type Reactions of Unmodified Ketones

Fujie Tanaka, Carlos F. Barbas, Maria Mifsud, Haile Zhang
J. Am. Chem. Soc. | 2006 | 10.1021/ja062950b

We report the development of direct catalytic, enantioselective, anti-selective Mannich-type reactions between unmodified ketones and α-imino esters under mild conditions. The reactions were performed using 5−10 mol % of (R)-3-pyrrolidinecarboxylic or...

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Catalytic Transamidation Reactions Compatible with Tertiary Amide Metathesis under Ambient Conditions

Nickeisha A. Stephenson, Samuel H. Gellman, Shannon S. Stahl, Jiang Zhu
J. Am. Chem. Soc. | 2009 | 10.1021/ja8094262

The carbon−nitrogen bond of carboxamides is extremely stable under most conditions. The present study reveals that simple zirconium− and hafnium−amido complexes are highly efficient catalysts for equilibrium-controlled transamidation reactions between...

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