Preparation of silyl enol ethers from acyloin derivatives using silyllithium reagents

Robertson, Bradley D.; Hartel, Aaron M.

doi:10.1016/j.tetlet.2008.01.133

Cited by 9 publications

(2 citation statements)

References 29 publications

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“…Preactivation/derivatization makes it easier to remove the hydroxy group but adds an extra chemical step to the synthesis. Various methods have been developed for this transformation over the past several years. − Selected known methods capable of removing hydroxy groups next to an activating group are captured in Figure . A method reported by Santigo et al uses photochemical conditions for the deoxygenation of acyloins in DMSO solvent, which works via a radical pathway .…”

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confidence: 99%

“…A method reported by Santigo et al uses photochemical conditions for the deoxygenation of acyloins in DMSO solvent, which works via a radical pathway . Some other methods are also reported that work via radical pathways. , A few more methods mediated by metals are known for the reductive elimination of the hydroxy group. − Each of these methods has its own advantages and limitations; to point out a few, some methods are limited only to acyloins, and some of them result in byproducts in selected substrates. − …”

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Direct Deoxygenation of α-Hydroxy and α,β-Dihydroxy Ketones Using a Silyl Lithium Reagent

Zade,

Gangnale,

Athawale

et al. 2023

J. Org. Chem.

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A reliable method for the one-step direct deoxygenation of α-hydroxy ketones has been developed using a silyl lithium reagent and acetic anhydride. The method is metal-catalyst-free and does not require prefunctionalization of the hydroxy group prior to its removal. Deoxygenation of different primary, secondary, and tertiary alcohols was carried out with up to 98% isolated yield. Additionally, double deoxygenation was achieved when the present method was applied to α,β-dihydroxy ketones to access the corresponding enones in a single step.

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confidence: 99%

Direct Deoxygenation of α-Hydroxy and α,β-Dihydroxy Ketones Using a Silyl Lithium Reagent

Zade,

Gangnale,

Athawale

et al. 2023

J. Org. Chem.

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The Brook Rearrangement

Yang

et al. 2020

Organic Reactions

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The Brook rearrangement describes the intramolecular silyl group migration from a carbon to an oxygen atom in a “through‐space” fashion. This feature has been extensively applied to develop numerous useful transformations of diverse organosilanes. Some representative examples include formal [3 + 2] and [4 + 3] annulations to construct diverse ring systems, syntheses of configurationally defined silyl enol ethers, multi‐component reactions by Brook rearrangement‐based ARC (anion relay chemistry), and various umpolung processes such as silyl benzoin condensations and sila‐Stetter reactions. This chapter presents a thorough overview of the Brook rearrangement. The scope and limitations are categorized according to the organosilane type. The mechanism and stereochemical course of this process are discussed, as is its application in the synthesis of complex natural products. The literature is covered up to the end of 2019.

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Brook Rearrangement

Sasaki¹,

Takeda²

2015

Molecular Rearrangements in Organic Synthesis

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Preparation of silyl enol ethers from acyloin derivatives using silyllithium reagents

Cited by 9 publications

References 29 publications

Direct Deoxygenation of α-Hydroxy and α,β-Dihydroxy Ketones Using a Silyl Lithium Reagent

Direct Deoxygenation of α-Hydroxy and α,β-Dihydroxy Ketones Using a Silyl Lithium Reagent

The Brook Rearrangement

Brook Rearrangement

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