Natural alkaloids and synthetic relatives as chiral templates of the Orito's reaction

The enantioselective hydrogenation of methyl or ethyl pyruvate over cinchona‐platinum catalyst system (Orito's reaction) is one of the most intensively studied heterogeneous catalytic asymmetric hydrogenation reactions. Studies aiming at systematic changes of the chiral template have played a c...

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Bibliographic Details
Published in:Chirality (New York, N.Y.) N.Y.), 2010-01, Vol.22 (1), p.3-15
Main Authors: Tálas, Emília, Margitfalvi, József L.
Format: Article
Language:English
Subjects:
activated ketones
Alkaloids
Alkaloids - chemistry
amines
aminoalcohols
Asymmetry
Catalysis
Catalysts
Chirality
cinchona alkaloids
Derivatives
enantioselective hydrogenation
heterogeneous catalysis
Hydrogenation
isocinchonines
Pt/Al2O3
Pyruvates
Stereoisomerism
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Summary:The enantioselective hydrogenation of methyl or ethyl pyruvate over cinchona‐platinum catalyst system (Orito's reaction) is one of the most intensively studied heterogeneous catalytic asymmetric hydrogenation reactions. Studies aiming at systematic changes of the chiral template have played a crucial role in creating hypotheses for the mechanism of Orito's reaction. It is very important to clarify which structural unit of the alkaloid takes part in the enantiodifferentiation, and learn about the role of the different structural units of chiral templates. In this article, we made an attempt to describe the behavior of natural alkaloids, their synthetic derivatives, and analogues as chiral templates in the heterogeneous catalytic asymmetric hydrogenation of activated ketones. Chirality, 2010. © 2009 Wiley‐Liss, Inc.
ISSN:0899-0042
1520-636X
DOI:10.1002/chir.20694