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Silylation-Based Kinetic Resolution of α-Hydroxy Lactones and Lactams

T. Maxwell Deaton, Yan Zhang, Maggie I. Moore, Sheryl L. Wiskur, Robert W. Clark
Org. Lett. | 2013 | 10.1021/ol402982w

A silylation-based kinetic resolution has been developed for α-hydroxy lactones and lactams employing the chiral isothiourea catalyst (−)-benzotetramisole and triphenylsilyl chloride as the silyl source. The system is more selective for lactones than lactams,...

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Scandium-Catalyzed Carbon−Carbon Bond-Forming Reactions of 3-Sulfanyl- and 3-Selanylpropargyl Alcohols

Arisa Sawa, Mitsuhiro Yoshimatsu, Teruhisa Yamamoto, Tokutaro Otani, Saki Matsuda
Org. Lett. | 2008 | 10.1021/ol801533p

The scandium-catalyzed substitution reactions of the phenylsulfanyl and phenylselanyl propargyl alcohols 3a−i and 7a−h regioselectively proceeded to give the propargylated compounds 4 and 8 in high yields.

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Photochemical Molecular Storage of Cl2, HCl, and COCl2: Synthesis of Organochlorine Compounds, Salts, Ureas, and Polycarbonate with Photodecomposed Chloroform

Ailing Zhang, Yuki Kuwahara, Akihiko Tsuda, Haruka Soma
Org. Lett. | 2012 | 10.1021/ol301356r

Chloroform is available as not only an organic solvent but also photochemical molecular storage for synthetically important chemicals such as Cl 2 , HCl, and COCl 2 . We have succeeded in synthesizing organochlorine compounds, hydrochloric salt of amines,...

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Coupling Reaction of Alkyl Chlorides with Silyl Enolates Catalyzed by Indium Trihalide

Yoshihiro Nishimoto, Makoto Yasuda, Akio Baba
Org. Lett. | 2007 | 10.1021/ol701684n

Indium(III) halide catalyzed not only the coupling of alkyl chlorides with silyl enolates derived from esters, ketones, and aldehydes to give a variety of α-alkylated carbonyl compounds but also one-pot, three-component reactions of aldehyde enolate, alkyl...

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Photolabile Protection of 1,2- and 1,3-Diols with Salicylaldehyde Derivatives

Vladimir V. Popik, Alexey P. Kostikov
Org. Lett. | 2008 | 10.1021/ol802141g

1,2- and 1,3-diols, including carbohydrates, can be readily caged as acetals of 5-methoxy- or 5-hydroxysalicylaldehydes. Irradiation of these acetals with 300 nm light results in their efficient (Φ = 0.2−0.3) cleavage, regenerating an aldehyde and a glycol in...

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Enantioselective Synthesis of Propargylamines through Zr-Catalyzed Addition of Mixed Alkynylzinc Reagents to Arylimines

John F. Traverse, Amir H. Hoveyda, Marc L. Snapper
Org. Lett. | 2003 | 10.1021/ol035138b

Addition of mixed alkynylzinc reagents to various arylimines is catalyzed by chiral amino acid-based ligand 1 and Zr(Oi-Pr) 4 ·HOi-Pr to afford chiral propargylamines in up to 90% ee. Oxidative removal of the o-anisidyl group affords the free amine, which can...

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Vinylogous Aldol Products from Chiral Crotylsilanes Obtained by Enantioselective Rh(II) and Cu(I) Carbenoid Si−H Insertion

James S. Panek, Yu Chen, Jie Wu
Org. Lett. | 2010 | 10.1021/ol100604m

Enantioenriched homoallylic ethers containing a α,β-unsaturated ester (syn-vinylogous aldol products) were directly accessed by Lewis acid catalyzed crotylation utilizing chiral silane 2. The reagents were prepared by enantioselective Si−H insertion to an...

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An Efficient Route to Alkyl Chlorides from Alcohols Using the Complex TCT/DMF

Giampaolo Giacomelli, Andrea Porcheddu, Lidia De Luca
Org. Lett. | 2002 | 10.1021/ol017168p

Efficient conversion of alcohols and β-amino alcohols to the corresponding chlorides (and bromides) can be carried out at room temperature in methylene chloride, using 2,4,6-trichloro[1,3,5]triazine and N,N-dimethyl formamide. This procedure can also be...

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Nickel-Catalyzed Carboxylation of Organozinc Reagents with CO2

Hidenori Ochiai, Minsul Jang, Hideki Yorimitsu, Koichiro Oshima, Koji Hirano
Org. Lett. | 2008 | 10.1021/ol800764u

An efficient nickel catalyst system for the carboxylation of organozinc reagents with CO 2 under very mild conditions has been developed. The catalyst system complements the conventional methods and enables the direct synthesis of various saturated...

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Synthesis of Biologically Active Amines via Rhodium−Bisphosphite-Catalyzed Hydroaminomethylation

Jerzy Klosin, John R. Briggs, Gregory T. Whiteker
Org. Lett. | 2005 | 10.1021/ol050848y

We report the use of a highly regioselective rhodium−bisphosphite catalyst for olefin hydroaminomethylation. This catalyst system was successfully applied in the synthesis of two biologically active tertiary amines, ibutilide and aripiprazole.

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Concise Synthesis of Reduced Propionates by Stereoselective Reductions Combined with the Kobayashi Reaction

Tatsuya Nakamura, Mio Harachi, Takaaki Kano, Yuki Mukaeda, Seijiro Hosokawa
Org. Lett. | 2013 | 10.1021/ol401406m

A concise and straightforward synthesis of 2,4,6-trimethyloctanoates was established by using the sequence of the vinylogous Mukaiyama aldol reaction and regio- and stereoselective reduction reactions. All isomers were obtained selectively in a few steps. The...

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Spirodiepoxide-Based Cascades: Direct Access to Diverse Motifs

Hiyun Kim, Lawrence J. Williams, Novruz G. Ahkmedov, Yue Zhang, Rojita Sharma, Madhuri Manpadi
Org. Lett. | 2011 | 10.1021/ol201101e

Allene epoxide formation/opening reaction sequences enabled direct access to diverse products. Described here are a single flask procedure for allene preparation and allene oxidation/derivatization reactions that give, among others, diendiol, diyndiol,...

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Concise Asymmetric Synthesis of Orthogonally Protected syn- and anti-1,3-Aminoalcohols

Dongeun Kim, Jae Seung Lee, Hyunsoo Han, Suk Bin Kong, Lucia Lozano
Org. Lett. | 2013 | 10.1021/ol303371u

Novel chiral binfunctional reagents V and ent-V undergo asymmetric aldehyde allylation followed by Ir(I)-catalyzed enantioselective allylic amidation to give orthogonally protected syn- and anti-1,3-aminoalcohols with complete control of absolute and relative...

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Manganese- or Iron-Catalyzed Homocoupling of Grignard Reagents Using Atmospheric Oxygen as an Oxidant

Alban Moyeux, Julien Buendia, Gérard Cahiez, Christophe Duplais
J. Am. Chem. Soc. | 2007 | 10.1021/ja075417k

Atmospheric oxygen was used for the first time as an oxidant in metal-catalyzed homocoupling of Grignard reagents. These manganese- or iron-catalyzed reactions are efficient, cheap, and eco-friendly. They are applicable to the large-scale synthesis of...

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Reactions of Alkyl Azides and Ketones as Mediated by Lewis Acids:  Schmidt and Mannich Reactions Using Azide Precursors

Gregory L. Milligan, Craig Mossman, Konstantinos A. Agrios, Klaas Schildknegt, Jeffrey Aubé, Pankaj Desai
J. Am. Chem. Soc. | 2000 | 10.1021/ja000490v

The Lewis acid-promoted reactions of alkyl azides with ketones can afford several products. Chief among these result from a Schmidt-like insertion of the azide into the carbon−carbon bond adjacent to the carbonyl group. Alternatively, an acid-promoted...

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Solid-Phase, Multicomponent Reactions of Methyleneaziridines:  Synthesis of 1,3-Disubstituted Propanones

Jean-François Margathe, Michael Shipman, Stephen C. Smith
Org. Lett. | 2005 | 10.1021/ol051953a

Polymer-supported methyleneaziridines undergo ring opening by Grignard reagents under copper catalysis to yield metalloenamines which are alkylated in situ to yield ketimines. Filtration and washing of these Merrifield resin-bound intermediates prior to...

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Palladium-Catalyzed Tandem Cyclization of Allenyl-Aldehydes and -Ketones with Aryl Iodides and Bu3SnSnBu3

Suk-Ku Kang, Young-Hwan Ha
Org. Lett. | 2002 | 10.1021/ol025557t

The arylative cyclization of allenyl-aldehydes with aryl iodides and hexa-n-butyldistannane to form substituted cyclopentanols and cyclohexanols by tandem palladium-catalyzed carbostannylation and allylation was achieved under mild conditions.

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Enantioselective α-Vinylation of Aldehydes via the Synergistic Combination of Copper and Amine Catalysis

Eduardas Skucas, David W. C. MacMillan
J. Am. Chem. Soc. | 2012 | 10.1021/ja303116v

The enantioselective α-vinylation of aldehydes using vinyl iodonium triflate salts has been accomplished via the synergistic combination of copper and chiral amine catalysis. These mild catalytic conditions provide a direct route for the enantioselective...

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Alkynylation of C−H Bonds via Reaction with Acetylenic Triflones1

Jianchun Gong, P. L. Fuchs
J. Am. Chem. Soc. | 1996 | 10.1021/ja953518p

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