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発表論文

Published in 2009

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Addition of allyl bromide to phenylacetylene catalyzed by palladium on alumina and its application to a continuous flow synthesis
Fukuyama, T., Kippo, T., Ryu, I., Sagae, T.
Research on Chemical Intermediates, 2009, 35, pp. 1053 - 1057
DOI: 10.1007/s11164-009-0069-x

The reaction of allyl bromide with phenylacetylene catalyzed by Pd/Al2O3 pellets and Pd/C powder was investigated. Bromoallylation of phenylacetylene took place to give a regioisomeric mixture of 1-bromo-substituted 1,4-dienes. The bromoallylation of phenylacetylene was successfully applied to a continuous flow synthesis using a stainless steel made column packed with Pd/Al2O3 pellets.

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Hydroruthenation triggered catalytic conversion of dialdehydes and keto aldehydes to lactones
Omura, S., Fukuyama, T., Murakami, Y., Okamoto, H., Ryu, I.
Chemical Communications, 2009, 44, pp. 6741 - 6743
DOI: 10.1039/B912850F

Lactonization of dialdehydes and keto aldehydes was effectively catalyzed by RuHCl(CO)(PPh3)3. A cascade lactonization sequence accompanied by cross-coupling with enones was also attained.

An automated-flow microreactor system for quick optimization and production: application of 10-and 100-gram order productions of a matrix metalloproteinase inhibitor using a Sonogashira coupling reaction
Sugimoto, A., Fukuyama, T., Rahman, M. T., Ryu, I.
Tetrahedron Lett. , 2009, 50, pp. 6364 - 6367
DOI: 10.1016/j.tetlet.2009.08.089

Sonogashira coupling reaction leading to a matrix metalloproteinase inhibitor was investigated using an automated microreactor system, which is a sequential temperature- and flow rate-programed reaction evaluation system. By repeating the use of this computer-controlled system four times, we were able to determine the optimal conditions and quickly apply them to a 10 g scale synthesis using the same microreactor system. The optimal conditions were also applied to a 100 g scale production by using another microflow system composed of a T-shaped micromixer (200 μm id) and a stainless tube reactor (2000 μm id and 20 m length). Total time spent for both optimization and production was as short as 50 h.

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Organocatalytic Enantioselective Synthesis of Nitrogen-Substituted Dihydropyran-2-ones, a Key Synthetic Intermediate of 1 beta-Methylcarbapenems
Kobayashi, S., Kinoshita, T., Uehara, H., Sudo, T., Ryu, I.
Org. Lett., 2009, 11, pp. 3934 - 3937
DOI: 10.1021/ol901544q

Organocatalytic enantioselective cycloadditions providing nitrogen-substituted dihydropyran-2-ones were developed in two catalytic systems. The (3R,4R)-product was a versatile intermediate in the synthesis of 1β-methylcarbapenem antibiotics.

Microflow Radical Carboaminoxylations with a Novel Alkoxyamine
Wienhoefer, I. C., Studer, A., Rahahman, M. D., Fukuyama, T., Ryu, I.
Org. Lett., 2009, 11, 11 pp. 2457 - 2460
DOI: 10.1021/ol900713d

Highly efficient thermal radical carboaminoxylations of various olefins by using the novel alkoxyamine A to give adducts of type B are described. It is reported that these radical addition reactions can be performed in a microflow reaction system. As compared to conventional batch reaction setup, significantly higher yields are obtained by running carboaminoxylations using the microflow system under analogous conditions.

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Microflow photo-radical reaction using a compact light source: application to the Barton reaction leading to a key intermediate for myriceric acid A
Sugimoto, A., Fukuyama, T., Sumino, Y., Takagi, M., Ryu, I.
Tetrahedron, 2009, 65, 8 pp. 1593 - 1598
DOI: 10.1016/j.tet.2008.12.063

The Barton reaction (nitrite photolysis) of a steroidal substrate 1, to give 2, a key intermediate for the synthesis of myriceric acid A, an endothelin receptor antagonist, was successfully carried out in a continuous microflow system using a Pyrex glass-covered stainless-steel microreactor having a one lane microchannel (Type A: 1000 μm width, 107 μm depth, 2.2 m length). We found that using a low-power black light (peak wavelength: 352 nm) and UV-LED light (peak wavelength: 365 nm) as the light source will suffice for the Barton reaction, creating a compact energy-saving photo-microreaction system. A multi-gram-scale production was attained using a multi-lane microreactor (Type B: 1000 μm width, 500 μm depth, 0.5 m length, 16 lanes) in conjunction with a black light.

 

 

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