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The Fluorine-Iminium Ion Gauche Effect: Proof of Principle and Application to Asymmetric Organocatalysis.
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I chose this paper because it demonstrated an interesting application of a bifunctional chiral phosphoric acid in enantioselective organocatalysisÂ via hydrogen bonding.
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Versatile Pd(OTf)2Â·2H2O-Catalyzed ortho-Fluorination Using NMP as a Promote
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The authors have developed a new protocol for efficient ortho-fluorination using Pd(OTf)2 Â·2H2O as the catalyst, N-fluoro-2,4,6- trimethylpyridinium triflate as the F+ source, and NMP as the crucial promoter. The triflamide directing group can be readily displaced bya wide range of heteroatom and carbon nucleophiles, thereby affording this fluorination protocol excellent versatility for synthetic applications.
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Ruthenium-Catalyzed Oxidation of Alcohols into Amides
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An intriguing paper which claims that NaH is an effective oxidation promoter. A series of benzylic alcohol oxidations are performed and the results seem surprising taking into account the usual reactivity of NaH. The authors claim that NaH is directly involved in the oxidation process and the fact that, NaH can be recovered at the end of the reaction, there is the suggestion that the reaction is catalytic. The article was picked up almost immediately on Paul Doherty's visual certexam manager 3.4.3 crack and has since become the most commented thread in the site's history. It's caused quite a stir.
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Angew.Chem.Int.Ed, 2009, 48, 2-6
An easy to read overview of key publications and recent developments in the metal-catalysed carboxylation of organometallic reagents
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Novel methodology for the formation of amide bonds under neutral conditions is described. Evidence is presented that the active acyl donors are thio FCMA intermediates, generated from the reactions of thioacids with isonitriles.
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Further investigations towards novel glycopeptide/-lactam heterodimers are reported. Employing a multivalent approach to drug discovery, vancomycin and cephalosporin synthons, 4, 2, 5 and 10, 18, 25 respectively, were chemically linked to yield heterodimer antibiotics. These novel compounds were designed to inhibit Grampositive bacterial cell wall biosynthesis by simultaneously targeting the principal cellular targets of both glycopeptides and -lactams. The positional attachment of both the vancomycin and the cephalosporin central cores has been explored and the SAR is reported. This novel class of bifunctional antibiotics 2836 all displayed remarkable potency against a wide range of Gram-positive organisms, including methicillin-resistant Staphylococcus aureus (MRSA). A subset of compounds, 29, 31 and 35 demonstrated excellent bactericidal activity against MRSA (ATCC 33591) and 31 and 35 also exhibited superb in vivo efficacy in a mouse model of MRSA infection. As a result of this work compound 35 was selected as a clinical candidate, TD-1792.
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Xiao Fu, Wei-Tian Loh, Yan Zhang, Tao Chen, Dr., Ting Ma, Hongjun Liu, Jianmin Wang, Choon-Hong Tan, Prof.
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Renat Kadyrov, Dr., René M. Koenigs, Dipl.-Chem., Claus Brinkmann, Dipl.-Chem., David Voigtlaender, Dr., Magnus Rueping, Prof. Dr.
AbstractValuable vicinal 1,2-diols can be prepared with high enantioselectivity by the asymmetric ruthenium-catalyzed hydrogenation of aryl- and alkyl-substituted -hydroxy ketones (see scheme). The ligands, which are distinguished by their modular construction, display excellent enantioface differentiation
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Comparison of two papers both of which give methods for the enantioselective boration of α,β-unsaturated carbonyl compounds. One paper studies cyclic compounds with the use of a copper catalyst, and the other acyclic compounds with a rhodium catalyst.
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Interesting synthesis of phenols from aryl iodides using a copper catalyst in comparison of the use of palladium catalysed conditions.
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Andrew T. Parsons and Jeffrey S. Johnson
A highly diastereoselective synthesis of 2,6-cis-disubstituted tetrahydropyrans (THPs) via Lewis acid-catalyzed formal [4 + 2] cycloaddition of donor−acceptor cyclobutanes and aldehydes has been developed. THP products are formed in up to 96% yield and 99:1 diastereoselectivity. Aromatic, cinnamyl, and aliphatic aldehydes are competent dipolarophiles in this system. This methodology was extended to a [[2 + 2] + 2] cycloaddition of 4-methoxystyrene, dimethyl methylidene malonate, and an aldehyde to furnish THPs directly without prior isolation of the cyclobutane.
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Various pyridines and pyrazines can be efficiently accessed from simple acyclic precursors using an intramolecular hydroamination/isomerization/aromatization sequence (see scheme). p-Toluenesulfonic acid (2 mol %) is used to catalyze this novel alkyne annulation, in which the oxime group allows for a subsequent redox-neutral aromatization step to occur.
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An efficient procedure for radical cyclization of alpha-bromo esters is reported. Reduction of the esters by DIBAL-H at low temperature gives aluminum acetals, which are cyclized in the presence of nBu3SnH and Et3B (see scheme). These one-pot conditions lead to polysubstituted gamma-lactols in high yields, and the mildness of the reaction conditions allows the preparation of acid-sensitive derivatives.
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The authors have taken substantial effort to identify the reaction intermediates involved in the catalytic cycle using sophisticated NMR spectroscopic experiments and have mapped the complete mechanism of the process.
One of the drawbacks in this process is the utilisation of expensive hydrosilanes as reducing reagents. However, the authors conclude in this paper that their ongoing research is focussed on using cheaper alternative hydride sources. Nevertheless, this protocol offers remarkable scope for new discoveries in chemical CO2 activation and fixation under metal-free conditions along with a possible hope for cheaper production of sustainable form of fuel in the era of global warming.
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Nickel-Catalyzed Regioselective Carbomagnesation of Methylenecyclopropanes through a Site-Selective Carbon–Carbon Bond Cleavage
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Rhenium- and Manganese-Catalyzed Synthesis of Aromatic Compounds from 1,3-Dicarbonyl Compounds and Alkynes
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