ChemInform Abstract: Biocatalytic Promiscuity: Lipase‐Catalyzed Asymmetric Aldol Reaction of Heterocyclic Ketones with Aldehydes.
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Abstract The desired products (III) are generally formed in low yields and low to moderate stereoselectivities.Keywords:
Aldol reaction
Aldol reaction
Methylene
Aldol condensation
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Asymmetric organocatalysis have been developed explosively, since the pioneering work on
proline-catalyzed asymmetric direct Aldol reaction reported by List, Barbas and coworkers[1].
Numerous organocatalysts have been designed and the stereochemistry of the Aldol reactions has been
significantly improved. However, organocatalytic direct aldol reactions of aldehydes with long-chain
acyclic aliphatic ketones have been less investigated[2][3]. Herein, we report diamine catalytic aldol
reaction of acyclic aliphatic ketones with aromatic aldehydes, providing high enantioselectivities. In
neat condition, these aldol reactions afforded Aldol products with 80–96% ee.
Aldol reaction
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Aldol reaction
Stereocenter
Lewis acid catalysis
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A cheap and simple aldol source for the aluminum-enolate in the catalytic aldol-transfer reaction opens a new pathway to prepare aldol adducts of ketones from aldehydes (see picture). The catalytic cycle is completed by the addition of the enolate to an aldehyde and the subsequent aldol exchange reaction with the cheap aldol (regenerates the catalyst).
Aldol reaction
Aldol condensation
Lewis acid catalysis
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The aldol reaction is one of the most powerful and versatile methods for the construction of C-C bonds. Traditionally, this reaction was developed in a stoichiometric version; however, great efforts in the development of chiral catalysts for aldol reactions were performed in recent years. Thus, in this review article, the development of metal-mediated chiral catalysts in Mukaiyama-type aldol reaction, reductive aldol reaction and direct aldol reaction are discussed. Moreover, the application of these catalysts in the total synthesis of complex molecules is discussed.
Aldol reaction
Stoichiometry
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The aldol reaction is one of the most important C-C bond forming reactions in organic synthesis, with a large application in the stereoselective synthesis of highly functionalized natural and synthetic substances. The first intermolecular proline-catalyzed direct aldol reaction was described by List and coworkers in 2000. Since then, the direct aldol reaction of aldehydes with ketones in the presence of a catalytic amount of L-proline and its structural derivatives have been evaluated for use in asymmetric catalytic direct aldol reactions. We will report here our preliminary results on the organocatalysts synthesis which will be applied in direct aldol reaction of aldehydes with ketones in aqueous media.
Aldol reaction
Organic Synthesis
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Asymmetric reactions are carried out by organocatalysis in many ways, making them very competitive and practical. One remarkable molecule, the amino acid proline, has become a crucial component in organocatalysis because of its ability to promote chemical transformations with high enantioselectivity. The following review discusses the contributions and recent advances in the field of asymmetric reactions catalyzed by l -proline and its derivatives. 1 Introduction 2 Asymmetric Aldol Reactions Catalyzed by
Aldol reaction
Michael reaction
Mannich reaction
Aldol condensation
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Aldol reaction
Stereocenter
Lewis acid catalysis
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Aldol reaction
Enamine
Addition reaction
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Aldol reaction
Aldol condensation
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