DOI: 10.1246/bcsj.45.3706. Asymmetric Hydrogenation of the C=N Bond. A Study of the Controlling Factors on the Stereoselectivity

Asymmetric Hydrogenation of the C=N Bond. A Study of the Controlling Factors on the Stereoselectivity

10.1246/bcsj.45.3706

Crossref journal-article

Oxford University Press (OUP)

Bulletin of the Chemical Society of Japan (286)

Abstract

Abstract Asymmetric catalytic hydrogenation of Schiff bases, i. e., N-(methylbenzylidene)-α-methylbenzylamine and N-(ethylbenzylidene)-α-ethylbenzylamine, using 10% palladium hydroxide on charcoal was studied to elucidate the steric course of the reaction. Effects of temperature, solvent, pressure, the amount of the catalyst, and ratio of the syn and anti isomers on the asymmetric hydrogenation were investigated. Temperature, solvent, the amount of the catalyst were found to be factors which controlled the stereoselectivity of the reaction. The hydrogenation of N-(methylbenzylidene)-α-methylbenzylamine always gave a higher asymmetric yield than that of N-(ethylbenzylidene)-α-ethylbenzylamine. Lowering the reaction temperature, lowering the polarity of the solvent, and decreasing the amount of the catalyst gave higher stereoselectivities in the hydrogenation reactions.

Bibliography

Yoshida, T., & Harada, K. (1972). Asymmetric Hydrogenation of the C=N Bond. A Study of the Controlling Factors on the Stereoselectivity. Bulletin of the Chemical Society of Japan, 45(12), 3706â3710.

Authors 2

Takao Yoshida (first)
Kaoru Harada (additional)

References 9 Referenced 20

Dates

Type	When
Created	19 years, 1 month ago (July 19, 2006, 10:05 p.m.)
Deposited	1 year, 7 months ago (Jan. 17, 2024, 4:11 a.m.)
Indexed	1 year, 7 months ago (Jan. 17, 2024, 7:02 p.m.)
Issued	52 years, 9 months ago (Dec. 1, 1972)
Published	52 years, 9 months ago (Dec. 1, 1972)
Published Online	19 years, 5 months ago (March 27, 2006)
Published Print	52 years, 9 months ago (Dec. 1, 1972)

Funders 0

None

BibTeX

@article{Yoshida_1972, title={Asymmetric Hydrogenation of the C=N Bond. A Study of the Controlling Factors on the Stereoselectivity}, volume={45}, ISSN={1348-0634}, url={http://dx.doi.org/10.1246/bcsj.45.3706}, DOI={10.1246/bcsj.45.3706}, number={12}, journal={Bulletin of the Chemical Society of Japan}, publisher={Oxford University Press (OUP)}, author={Yoshida, Takao and Harada, Kaoru}, year={1972}, month=dec, pages={3706–3710} }

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