With Tag: General Organic Chemistry

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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,...


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.


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,...


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...


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...


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...


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...


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...


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...


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.


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...


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,...


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...


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...


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...


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...


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.


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...


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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