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Synlett - published by Thieme
Accounts and Rapid Communications in Synthetic Organic Chemistry: SYNLETT is an international journal reporting research results and trends in synthetic organic chemistry in short personalized reviews and preliminary communications.
SynlettDOI: 10.1055/s-0031-1291005Biomimetic recycling of the expensive cofactors NAD(P)H/NAD(P)+ and their models is a promising area in bio-inspired synthesis. This paper highlights the recent advances in the in situ regeneration of the oxidized cofactors NAD(P)+ through oxidation of cofactors NAD(P)H in the presence of an alcohol dehydrogenase by means of dioxygen and a synthetic Fe(III) porphyrin as a biomimetic NAD(P)H oxidase or flavin as catalyst, and biomimetic in situ regeneration of the expensive NAD(P)H models Hantzsch esters (HEH) and 9,10-dihydrophenanthridine (DHPD) by transition-metal and chiral Brønsted acid catalyzed relay asymmetric hydrogenation.1. Introduction2. Biomimetic in situ Regeneration of NAD(P)+3. Biomimetic in situ Regeneration of Hantzsch Esters (HEH)4. Biom...
SynlettDOI: 10.1055/s-0031-1290672AbstractHeterocyclic phosphines have long been used as unique and efficient ligands for palladium-catalyzed cross-coupling reactions. The simplest ligand, trifurylphosphine, has become one of the most classical heterocyclic phosphines for coupling reactions since its first application in the Stille coupling reaction in 1988. In recent decades, palladium catalyst systems derived from highly diverse and innovative heterocyclic phosphines have shown excellent catalytic activities in cross-coupling reactions. In this account, we discuss the recent development and applications of heterocyclic phosphine ligands, highlighting the synthetic pathways used to prepare the ligands. The sections are categorized by the different palladium-catalyzed cross-coupling method...
SynlettDOI: 10.1055/s-0031-1290938A new palladium(II) complex based on N,N-dimethylethanolamine, (SP-4-1?)-bis[N,N-dimethylaminoethoxy-kN,O]palladium(II) which coordinates with two moles of AcOH, has been synthesized. The structure of the complex has been established by X-ray diffraction analysis. Using this complex as a catalyst, a series of conjugated enynes were successfully synthesized by Sonogashira cross-coupling reaction in the absence of co-catalyst CuX and any ligand at room temperature during 20 hours affording the corresponding products in moderate to excellent yields. The optimized catalytic systems are tolerant in the presence of a broad variety of functional groups in the substrates. The catalytic system was found to be ineffective for vinyl chloride. Moreover, it was found...
SynlettDOI: 10.1055/s-0031-1290193This account summarizes the results of recent studies conducted in our group on the development of chiral thiourea/cinchona and Brønsted acid derived bifunctional organocatalysts. Selected asymmetric organocatalytic transformations were targeted to obtain enantioenriched bioactive products. Special emphasis was placed on the preparation of environmentally friendly anti-plant viral agents such as enantiomerically enriched ?-aminophosphonates and methods to assess the enantiomeric purity of these products on selected chiral stationary phases. The review also tries to delineate the underlying mechanism of various asymmetric transformations by BINOL-phosphoric acid-induced activation of imines and to make unambiguous assignments of the absolute configuration...
SynlettDOI: 10.1055/s-0031-1290486This Account describes our work on highly electrophilic ?-carbonyl cations featuring propargyldicobalt cations, cycloheptynedicobalt complexes, and the interconnection between the two systems.1 Introduction2 ?-Carbonyl Cations via Iron Allyl Cations3 ?-Carbonyl Cations via Propargyldicobalt Cations3.1 Synthesis of Velloziolide3.2 Synthesis of Microstegiol4 Synthesis of Cycloheptynedicobalt Complexes4.1 Synthesis via ?-Carbonyl Cations4.2 Cycloheptynedicobalt Complexes via [4+3] Cycloaddition Reactions4.3 Cycloheptynedicobalt Complexes via Ring-Closing Metathesis4.4 Cycloaddition Reactions on Cycloheptynedicobalt Complexes4.5 Cycloheptynedicobalt Complexes via Intramolecular Nicholas Reactions5 Dehydrotropylium Ion Co2(CO)6 Complex6 Final Comments[....
We describe our successful efforts for the translation of our research strategy that was focused on a broad structural modification of the natural product epothilone B, to the production of the distinct drug candidate sagopilone in a kg scale. By a direct comparison of the research and development procedures we address some important aspects to be considered for an up-scaling process.1 Introduction and Concept2 Preparation of Building Block A2.1 Research Sequence
A1--A3-A4-A5-A6-A7-A8-A9- A10-(A12-)A132.2 Development Sequence A11-A12-A133 Preparation of Building Block B3.1 Research Sequence B1-B2-B3-B4-(B6-B7)-B9-B103.2 Development Sequence B1-B2-B3-B4-B5-B8-B104 Preparation of Building Block C4.1 Research Sequence
C1-C2-C3-C4-C6-C7-C9-C10-C11-C124.2 Development Sequence C1-C2-C5-C8-C9-...
SynlettDOI: 10.1055/s-0031-1290616AbstractPreviously, the outcome of the alkylation of cyclen (1,4,7,10-tetraazacyclododecane) with arginine-modified electrophiles was found to be dependent on the solvent used for the reaction as well as on the structure of the electrophile. Herein, we report the alkylation of the related nitrogen macrocycles, TACN (1,4,7-triazacyclononane), cyclam (1,4,8,11-tetraazatetradecane) and the smaller cycles piperidine and piperazine with arginine-modified electrophiles. The products of peralkylation predominate for piperazine and TACN while the product of trialkylation is isolated as a sole product, when cyclam is used as a substrate for the alkylation. The results reported herein provide useful information for chemists involved in the design and synthesis of li...
SynlettDOI: 10.1055/s-0031-1290620AbstractAsymmetric processes, taking place via the intermediacy of chiral oxonium ions arising from intramolecular haloetherification reactions of chiral ene- and diene-acetals of optically pure C2-symmetric hydrobenzoine, have been developed. A novel, double intramolecular haloetherification process was observed. The asymmetric reactions developed in this effort were applied to the synthesis of several natural products, including solenopsin A, (cis-6-methyltetrahydropyran-2-yl)acetic acid, the pheromone of the wasp Paravespula vulgaris, rubrenolide, rubrynolide, scyphostatin, cryptocaryone, Sch 642305, and clavolonine. The strategies used in these syntheses involved a new concept called ‘chiral auxiliary multiple-use methodology'. In addition, intramole...
SynlettDOI: 10.1055/s-0031-1290530AbstractThis Account describes our research over the past decade in the asymmetric alkyne addition to aldehydes to generate optically active propargylic alcohols. Our methods employ a dialkylzinc reagent to react with a terminal alkyne to form an alkynylzinc nucleophile, and can be grouped into the BINOL-catalyzed reactions and the functionalized BINOL catalyzed reactions. We first describe the development of the BINOL-ZnEt2-Ti(Oi-Pr)4 catalyst system, and its modification through the use of Lewis base additives to form the alkynylzinc at room temperature. The substrate scope compatible with these methods and the enantioselectivities achieved are discussed. We then describe the functionalized BINOL and H8BINOL catalyst systems, which can be further divided...
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