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Organozinc Reagents (organozinc + reagent)
Selected AbstractsChemInform Abstract: Kinetic Resolution of an Organozinc Reagent: In situ Formation of an Enantioenriched Allenylzinc Species.CHEMINFORM, Issue 37 2001Jean-F. Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a "Full Text" option. The original article is trackable via the "References" option. [source] Ketopinic Acid Derived Bis(hydroxy amides) as Cheap, Chiral Ligands for the Enantioselective Ethylation of Aromatic AldehydesEUROPEAN JOURNAL OF ORGANIC CHEMISTRY, Issue 9 2010Tomás de las Casas Engel Abstract Readily accessible, C2 - and pseudo- C2 -symmetric bis(hydroxy amides), derived from commercially available (+)-ketopinic acid and protic diamines, are promising, cheap, chiral ligands for the synthetically valuable, enantioselective addition of organozinc reagents to carbon electrophiles. A series of ligands of this type, having key structural differences, has been synthesized and tested in the enantioselective ethylation of benzaldehydes and (E)-cinnamaldehyde, in order to gain information on the origin of ligand efficiency. The results obtained allow for the definition of a privileged structural pattern for the design of improved cheap ligands and support interesting models proposed for both the acting catalytic species and the controlling transition states. The most efficient ligands proved to be less efficient than commercially available (,)-MIB; nevertheless, an impressive efficiency level was obtained, which should sustain interest in this cheap type of ligands. [source] A catalytic route to acyclic chiral building blocks: Applications of the catalytic asymmetric conjugate addition of organozinc reagents to cyclic enonesISRAEL JOURNAL OF CHEMISTRY, Issue 4 2001Richard B. C. Jagt Through the Cu-phosphoramidite-catalyzed asymmetric conjugate addition a number of chiral cyclic enones are available with high ee. Here we report the sequential conjugate addition to these enones as a route towards multisubstituted chiral cyclic ketones. A subsequent Baeyer,Villiger oxidation followed by ring-opening results in various linear synthons containing multiple stereocenters. This procedure represents a short, catalytic, and highly enantioselective route to a variety of acyclic chiral building blocks. [source] Regio- and stereospecific synthesis of polysubstituted alkenes by carbozincation of acetylenic sulfonesAPPLIED ORGANOMETALLIC CHEMISTRY, Issue 7 2009Meihua Xie Abstract Tri- or tetrasubstituted alkenes with various substituents can be constructed regio- and stereospecifically by treatment of acetylenic sulfones with organozinc reagents in tetrahydrofuran followed by hydrolysis or coupling with halohydrocarbon. Copyright © 2009 John Wiley & Sons, Ltd. [source] Cosolvent-promoted electrophilic amination of organozinc reagentsAPPLIED ORGANOMETALLIC CHEMISTRY, Issue 6 2009Tahir Da, kapan Abstract In this study, we aimed to develop a simple and efficient method for the electrophilic amination of organozinc reagents. For this reason, 12 cosolvents were screened in the electrophilic amination of ordinary organozinc reagents. By the use of a cosolvent, an easily applicable and high-yielding method for the preparation of arylamines by electrophilic amination of arylzinc reagents was developed. Copyright © 2009 John Wiley & Sons, Ltd. [source] ChemInform Abstract: Silver-Catalyzed Benzylation and Allylation of Tertiary Alkyl Bromides with Organozinc Reagents.CHEMINFORM, Issue 42 2010Yukihiro Mitamura Abstract Silver salts catalyze the benzylation and allylation of tertiary alkyl bromides with organozinc reagents. [source] Identification of a Highly Efficient Alkylated Pincer Thioimido,Palladium(II) Complex as the Active Catalyst in Negishi CouplingCHEMISTRY - A EUROPEAN JOURNAL, Issue 17 2009Jing Liu Dr. Abstract PdIIate complex: A novel alkylated pincer thioimido,Pd complex generated from a catalyst precursor and basic organometallic reagents (RM) was observed by in situ IR, 1H,NMR, and 13C,NMR spectroscopies for the first time and proved to be the active catalyst in stoichiometric and catalytic reactions of aryl iodides with RM (see scheme). The catalyst, as an electron-rich PdII species, promoted the Negishi coupling of aryl iodides and alkylzinc reagents with high efficiency, even at low temperatures (0 or ,20,°C). The induction period of Negishi coupling catalyzed by pincer thioamide,palladium complex 1 was investigated. A heterogeneous mechanism was excluded by kinetic studies and comparison with Negishi coupling reactions promoted by Pd(OAc)2/Bu4NBr (a palladium,nanoparticle system). Tetramer 2 was isolated from the reaction of 1 and organozinc reagents. Dissociation of complex 2 by PPh3 was achieved, and the structure of resultant complex 8 was confirmed by X-ray diffraction analysis. A novel alkylated pincer thioimido,PdII complex, 7, generated from catalyst precursor 1 and basic organometallic reagents (RM), was observed by in situ IR, 1H,NMR, and 13C,NMR spectroscopy for the first time. The reaction of 7 with methyl 2-iodobenzoate afforded 74,% of the cross-coupled product, methyl 2-methylbenzoate, together with 60,% of PdII complex 2. Furthermore, the catalyst, as an electron-rich PdII species, efficiently promoted the Negishi coupling of aryl iodides and alkylzinc reagents without an induction period, even at low temperatures (0,°C or ,20,°C). To evaluate the influence of the catalyst structure upon the induction period, complex 9 was prepared, in which the nBu groups of 1 were displaced by more bulky 1,3,5-trimethylphenyl groups. Trimer 10 was isolated from the reaction of complex 9 and basic organometallic reagents such as CyZnCl or CyMgCl (Cy: cyclohexyl); this is consistent with the result obtained with complex 1. The rate in the induction period of the model reaction catalyzed by 9 was faster than that with 1. Plausible catalytic cycles for the reaction, based upon the experimental results, are discussed. [source] | ||||||||||||||||||||||