- Stereocontrolled Synthesis of (+)-Plagiogyrin A
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Plagiogyrin A (1) was first isolated from the fronds of Plagiogyria matsumureana. Structurally, it features an α-ketoaldehyde functional group in its hemiacetal form, fused in a cis-substituted lactone ring. We have successfully synthesized the skeleton o
- Shi, Yunlong,Pierce, Joshua G.
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- Efficient Heck arylations of cyclic and acyclic acrylate derivatives using arenediazonium tetrafluoroborates. A new synthesis of the antidepressant drug (±)-paroxetine
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The Heck arylation of acyclic- and cyclic-substituted acrylates using several arenediazonium tetrafluoroborates was investigated. Arylations were carried out under aerobic, ligand-free conditions to provide the corresponding substituted acrylates in moderate to high isolated yields. Heck arylations were usually completed in less than 2 h in refluxing methanol. The aza-endocyclic acrylate derivative 11a was converted into the antidepressant drug (±)-paroxetine in a concise new route in good overall yield.
- Pastre, Julio Cezar,Correia, Carlos Roque Duarte
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- Phosphine-Catalyzed Cross-Coupling of Benzyl Halides and Fumarates
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A phosphine-catalyzed olefinic cross-coupling between benzyl halides and fumarates is described, which affords trisubstituted alkenes in good yields and excellent E-selectivity under metal-free conditions. Mechanistic studies suggest a catalytic cycle involving phosphorus ylide formation, Michael addition, water-assisted hydrogen transfer, and phosphine elimination.
- Yan, Tingting,Babu, Kaki Raveendra,Wu, Yong,Li, Yang,Tang, Yuhai,Xu, Silong
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supporting information
p. 4570 - 4574
(2021/06/28)
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- Benign Arylations of Dimethyl Itaconate via Heck–Matsuda Reaction Utilizing in-Situ Generated Palladium on Aluminum Oxide
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In situ generated palladium on aluminum oxide provides an active and efficient catalytic system for the preparation of arylmethylidene succinates using the Heck–Matsuda reaction. Beside the monoarylation the first examples of the biarylation of these mono
- Matelien?, Lauryna,Knaup, Jan,von Horsten, Frank,Gu, Xiaoting,Brunner, Heiko
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supporting information
p. 127 - 135
(2020/01/30)
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- Silver sequestration of halides for the activation of Pd(OAc)2 catalyzed Mizoroki-Heck reaction of 1,1 and 1,2 - Disubstituted alkenes
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A ligand free catalytic system consisting of Pd(OAc)2 (cat) and stoichiometric quantities of silver salts, AgOAc or AgBF4, exhibit high efficiency in the Mizoroki-Heck arylation, transforming aryl iodides and 1,1 as well as 1,2 disubstituted alkenes into 1,1,2 – trisubstituted aryl alkenes in excellent yields in very short reaction times.
- Bangar, Pronnoy G.,Jawalkar, Priyanka R.,Dumbre, Swapnil R.,Patil, Dharmaraj J.,Iyer, Suresh
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- Novel Base-Free Catalytic Wittig Reaction for the Synthesis of Highly Functionalized Alkenes
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A highly efficient catalyst system for base-free catalytic Wittig reactions has been developed and optimized. Initially, several potential (pre)catalysts as well as different silanes as reducing agents were screened. A system based on a readily available
- Schirmer, Marie-Luis,Adomeit, Sven,Spannenberg, Anke,Werner, Thomas
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supporting information
p. 2458 - 2465
(2016/02/12)
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- A phosphane-free catalyst system for the heck arylation of disubstituted alkenes: Application to the synthesis of trisubstituted olefins
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A new general procedure for the Heck arylation of disubstituted olefins is described. This procedure allows, in many instances, the stereoselective synthesis of trisubstituted olefins. Trisubstituted olefins are easily accessible under mild reaction condi
- Guertler, Christoph,Buchwald, Stephen L.
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p. 3107 - 3112
(2007/10/03)
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- Synthesis of Enol Lactones of 3-Aroyl-2-(thienylmethylene)-propionic Acids and their Conversion into the Corresponding 4-Arylbenzothiophene-6-carboxylic Acids
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Heterocyclic aldehydes such as 2-thiophenecarbaldehyde (1) condense with 3-aroylpropionic acids 2 or their sodium salts to give the enol lactones 3a-d of 3-aroyl-2-(2-thienylmethylene)propionic acids.Isomerization of 3a-d leads to the corresponding 4-aryl
- Guirguis, Nadia R.,Awad, Boshra M.,Saad, Hanaa A.
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p. 1003 - 1011
(2007/10/02)
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- Annelation Reactions of N-Heterocycles to Condensed Pyridones with Bridgehead Nitrogen
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The Horner-Wittig reaction of aromatic and heteroaromatic aldehydes with phosphono succinates gives the methylenesuccinates 2a-m and 4a-k in satisfactory yields.The compounds obtained have the E-configuration, as shown by 1H-NMR-spectroscopic and by chemi
- Linke, Siegfried,Kurz, Juergen,Lipinski, Dietmar,Gau, Wolfgang
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p. 542 - 556
(2007/10/02)
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