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Kosuke Namba

Publications and source records attributed to Kosuke Namba.

5 recordsLinked to original sources

A new method for translating the asymmetric Ni/Cr-mediated coupling reactions from stoichiometric to catalytic.

[reaction: see text] A new method has been developed for effectively translating the degree of asymmetric induction and the chemical yield achieved in the stoichiometric asymmetric Ni/Cr-mediated coupling to a catalytic asymmetric process via a chiral sulfonamide ligand. It has also been shown that the Ni catalyst plays a central role. Among a number of the Ni catalysts, the 2,9-dimethylphenanthroline/NiCl(2) complex (7) has been found to be the most effective.

Benzene Derivatives↗

Surprisingly efficient catalytic Cr-mediated coupling reactions.

[reaction: see text] With use of 1 mol % of Cr catalyst 5, surprisingly efficient Cr-mediated couplings of aldehydes with various types of nucleophiles have been realized. The catalyst set of Cr catalyst 5 and Ni catalyst 4 is used for alkenylation, alkynylation, and arylation, whereas the catalyst set of Cr catalyst 5 and CoPc (cobalt phthalocyanine) is used for 2-haloallylation, alkylation, and propargylation. Only the Cr catalyst 5 is required for allylation. The reaction rates in DME and THF have been found significantly faster than that in MeCN.

Aldehydes↗

Catalytic Ni/Cr-mediated macrocyclization without use of high-dilution techniques.

The feasibility of catalytic Ni/Cr-mediated macrocyclization was demonstrated for the two substrates chosen from the halichondrin area. With 5 mol % of Ni and Cr catalysts, the macrocyclization was realized without use of high-dilution techniques. The reported method has a number of appealing features, including user-friendliness, easy workup, apparent scalability, and cost-effectiveness. In addition, all the required reagents are commercially available or obtainable in one or two steps from commercially available chemicals.

Catalysis↗

New catalytic cycle for couplings of aldehydes with organochromium reagents.

[reaction: see text] A new catalytic cycle has been developed to effect all three subgroups of Cr-mediated couplings, i.e., (1) Ni/Cr-mediated alkenylation, alkynylation, and arylation, (2) Co/Cr-mediated 2-haloallylation, alkylation, and propargylation, and (3) Cr-mediated allylation. In the presence of chiral sulfonamide ligands, good asymmetric inductions can be achieved for some of the Ni/Cr-mediated alkenylation, Co/Cr-mediated 2-haloallylation and propargylation, and Cr-mediated allylation.

Alcohols↗

A simple but remarkably effective device for forming the C8-C14 polycyclic ring system of halichondrin B.

A simple device consisting of two ion-exchange columns, two alumina-based filters, and a pump (Figure 1) was assembled to form the C8-C14 polycyclic ring system present in the halichondrin B class of marine natural products. The effectiveness of this device was tested for three substrates. In each case, the desired polycyclic ketal 3, 5, or 7 was obtained almost quantitatively in a single operation.

Aldehydes↗