Direct Catalytic Asymmetric Aldol-Type Reaction of Aldehydes with Ethyl Diazoacetate

Asymmetric aldol reactions are a powerful method for the construction of carbon-carbon bonds in an enantioselective fashion. Historically this reaction has been performed in a stoichiometric fashion to control the various aspects of chemo-, diastereo-, regio- and enantioselectivity, however, a more atom economical approach would unite high selectivity with the use of only a catalytic amount of a chiral promoter. This critical review documents the development of direct catalytic asymmetric aldol methodologies, including organocatalytic and metal-based strategies. New methods have improved the reactivity, selectivity and substrate scope of the direct aldol reaction and enabled the synthesis of complex molecular targets

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“…332 The reaction was applied to aryl, heteroaryl, styrenyl, and alkyl aldehydes. The adducts 270 were obtained in 47–82% yield and in 53–87% ee.…”

Section: Metal-catalyzed Aldol Reactionsmentioning

confidence: 99%

The direct catalytic asymmetric aldol reaction

2010

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“…Column chromatography purification of the diazo diol followed by oxidation with dimethyl dioxirane resulted in pure racemic DPD and analogs 50 in moderate to high yields (up to 39% overall yield). Potentially, enantioselective diazo Aldol reactions, developed by Trost [75] and others [76] could be adopted to make enantio-enriched DPD and analogs, using Sintim’s methodology. To date, Sintim’s synthesis has produced many C1-modified AI-2 analogs (with linear, branched, cyclic, and, aromatic C1 groups).…”

Section: Synthesis Of Ai-2mentioning

confidence: 99%

Small Molecule Inhibitors of AI-2 Signaling in Bacteria: State-of-the-Art and Future Perspectives for Anti-Quorum Sensing Agents

Guo

Gamby

Zheng

et al. 2013

IJMS

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Bacteria respond to different small molecules that are produced by other neighboring bacteria. These molecules, called autoinducers, are classified as intraspecies (i.e., molecules produced and perceived by the same bacterial species) or interspecies (molecules that are produced and sensed between different bacterial species). AI-2 has been proposed as an interspecies autoinducer and has been shown to regulate different bacterial physiology as well as affect virulence factor production and biofilm formation in some bacteria, including bacteria of clinical relevance. Several groups have embarked on the development of small molecules that could be used to perturb AI-2 signaling in bacteria, with the ultimate goal that these molecules could be used to inhibit bacterial virulence and biofilm formation. Additionally, these molecules have the potential to be used in synthetic biology applications whereby these small molecules are used as inputs to switch on and off AI-2 receptors. In this review, we highlight the state-of-the-art in the development of small molecules that perturb AI-2 signaling in bacteria and offer our perspective on the future development and applications of these classes of molecules.

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“…Wang and coworkers first demonstrated the utility of diazoesters as nucleophiles in an asymmetric aldol reaction. 9 A BINOL derived zirconium catalyst afforded the desired products in 53%–83% ee, where aromatic aldehydes resulted in higher levels of enantioinduction than aliphatic aldehydes. Arai and coworkers employed a chiral phase transfer cinchonidium derived catalyst that afforded the desired products in 0%–81% ee and demonstrated the utility of the resulting products in accessing α-amino acids.…”

Section: Resultsmentioning

confidence: 99%

Development of the Enantioselective Addition of Ethyl Diazoacetate to Aldehydes: Asymmetric Synthesis of 1,2-Diols

et al. 2012

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A novel synthetic strategy towards the asymmetric synthesis of vicinal diols bearing a tertiary center is presented. The method encompasses the dinuclear Mg-catalyzed asymmetric addition of ethyl diazoacetate into several aldehydes, oxidation of the diazo functionality, and diastereoselective alkyl transfer of various organometallics into the resulting chiral β-hydroxy-α-ketoesters to afford a diverse range of 1,2-diols in high yield, diastereoselectivity, and chirality transfer.

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Direct Catalytic Asymmetric Aldol-Type Reaction of Aldehydes with Ethyl Diazoacetate

Abstract: The direct aldol-type condensation of aldehydes with ethyl diazoacetate catalyzed by the chiral complex of BINOL derivatives-Zr(O(t)Bu)(4) gave beta-hydroxy alpha-diazo carbonyl compounds with moderate enantioselectivities (53-87% ee). [reaction: see text]

Cited by 82 publications

References 7 publications

The direct catalytic asymmetric aldol reaction

The direct catalytic asymmetric aldol reaction

Small Molecule Inhibitors of AI-2 Signaling in Bacteria: State-of-the-Art and Future Perspectives for Anti-Quorum Sensing Agents

Development of the Enantioselective Addition of Ethyl Diazoacetate to Aldehydes: Asymmetric Synthesis of 1,2-Diols

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