DOI: 10.1002/adsc.200390020. Non‐Linear Effect of Modifier Composition on Enantioselectivity in Asymmetric Hydrogenation over Platinum Metals

Non‐Linear Effect of Modifier Composition on Enantioselectivity in Asymmetric Hydrogenation over Platinum Metals

10.1002/adsc.200390020

Crossref journal-article

Wiley

Advanced Synthesis & Catalysis (311)

Abstract

AbstractProminent non‐linear behavior was observed when mixtures of cinchona alkaloids were applied as chiral modifiers in enantioselective hydrogenations over Pt/Al2O3 and Pd/TiO2. The phenomenon is traced to differences in the strength and geometry of alkaloid adsorption on the metal surface. In ethyl pyruvate hydrogenation under close to ambient conditions the weaker adsorbing quinidine (QD) outperformed the generally preferred modifier cinchonidine (CD) and afforded the highest ee (96–98%) at 1–5 bar. In the partial hydrogenation of 4‐methoxy‐6‐methyl‐2‐pyrone to the dihydro derivative 4 CD gave 73% ee to (S)‐4 and QD provided 72% ee to (R)‐4, and still the alkaloid mixture containing less than 5 mol % CD afforded 15% ee to (S)‐4. This non‐linear behavior may be advantageous in asymmetric synthesis as low purity chiral compounds can be applied as efficient modifiers for Pt or Pd.

Bibliography

Huck, W., Mallat, T., & Baiker, A. (2003). NonâLinear Effect of Modifier Composition on Enantioselectivity in Asymmetric Hydrogenation over Platinum Metals. Advanced Synthesis & Catalysis, 345(1â2), 255â260. Portico.

Authors 3

Wolf‐Rüdiger Huck (first)
Tamas Mallat (additional)
Alfons Baiker (additional)

References 44 Referenced 43

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Dates

Type	When
Created	22 years, 7 months ago (Jan. 24, 2003, 11:09 a.m.)
Deposited	1 year, 11 months ago (Aug. 31, 2023, 9:49 a.m.)
Indexed	2 months ago (June 27, 2025, 3:44 p.m.)
Issued	22 years, 7 months ago (Jan. 1, 2003)
Published	22 years, 7 months ago (Jan. 1, 2003)
Published Online	22 years, 7 months ago (Jan. 21, 2003)
Published Print	22 years, 7 months ago (Jan. 1, 2003)

Funders 0

None

BibTeX

@article{Huck_2003, title={Non‐Linear Effect of Modifier Composition on Enantioselectivity in Asymmetric Hydrogenation over Platinum Metals}, volume={345}, ISSN={1615-4169}, url={http://dx.doi.org/10.1002/adsc.200390020}, DOI={10.1002/adsc.200390020}, number={1–2}, journal={Advanced Synthesis & Catalysis}, publisher={Wiley}, author={Huck, Wolf‐Rüdiger and Mallat, Tamas and Baiker, Alfons}, year={2003}, month=jan, pages={255–260} }

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