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Journal of the American Chemical Society (ACS …

Olefin metathesis catalysts for controlling the formation of trisubstituted macrocyclic Z alkenes have been developed. The most effective complexes are Mo alkylidenes with a pentafluorophenylimido group and two large aryloxide ligands. The macrocyclic lactone precursor to anticancer agents epothilones B and D is obtained in 73 % yield and 91 % Z selectivity in less than 6 hours at room temperature.

ThalesNano Nanotechology Inc - Publications

Rhodium-Catalyzed Asymmetric 1,4-Addition and Its …

Alkenyl halides are effective as electrophiles when paired with nucleophiles that form stable -alkenes, such as amides and azoles. The reactivity of alkenyl halides is largely unaffected by electron-donating and -withdrawing substituents. Monosubstituted, disubstituted, and trisubstituted alkenes have all been employed with success. Retention of configuration of the alkene is generally observed, suggesting an OA/RE mechanism (Eq. 7). Use of a ligand is generally necessary in reactions of alkenyl halides.

24/07/2003 · Tamio Hayashi was born in Gifu, Japan, in 1948

Selective catalytic synthesis of Z-olefins has been challenging. Here we describe a method to produce 1,2-disubstituted olefins in high Z selectivity via reductive cross-coupling of alkyl halides with terminal arylalkynes . The method employs inexpensive and non-toxic catalyst (iron(II) bromide) and reductant (zinc). The substrate scope encompasses primary, secondary, and tertiary alkyl halides, and the reaction tolerates a large number of functional groups. The utility of the method is demonstrated in the synthesis of several pharmaceutically relevant molecules. Mechanistic study suggests that the reaction proceeds through an iron-catalyzed anti-selective carbozincation pathway.

He graduated from Kyoto University in 1970