Selective reduction of α,β-epoxyketones to β-hydroxyketones using silyllithium reagents

Reynolds, Samantha C.; Wengryniuk, Sarah E.; Hartel, Aaron M.

doi:10.1016/j.tetlet.2007.07.095

Cited by 17 publications

(1 citation statement)

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“…[3][4][5][6][7] Several methods are known for the synthesis of β-amino ketones from the ring opening of aziridines. A literature survey shows the few reducing agents, including Raney nickel in ethanol, 8 Pearlman's catalyst [Pd(OH) 2 /C], 9 Adam's catalyst (PtO 2 /HCO 2 H), 10 sodium borohydride, 11 tributyltin hydride, 12 poly(methylhydrosiloxane) (PMHS), 13 silyllithium reagents, 14 magnesium 15 and lithium 16 metal reagents, titanium tetraiodide, 17 samarium(II) iodide 18 and visible-light photoredox ruthenium catalysts, 19 for the reductive ring opening of aziridines. None of these methods, however, result in a direct reduction reaction of N-H aziridines to give derivatives of β-carbamato ketones.…”

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Synthesis of tert-Butyl 1,3-Diaryl-3-oxopropylcarbamates by a Regiocontrolled Reduction of Ketoaziridines

Samimi

Yamin²,

Saberi

2014

Synthesis

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A new, convenient approach for the reductive ring opening of N-H ketoaziridines is described. Treatment of N-H ketoaziridines with di-tert-butyl dicarbonate [(Boc) 2 O] in the presence of sodium iodide and nickel(II) chloride results in the corresponding tert-butyl 1,3-diaryl-3-oxopropylcarbamates by a regiocontrolled reaction. The structure of the regioisomeric product was confirmed by X-ray crystal structure analysis.

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confidence: 99%

Synthesis of tert-Butyl 1,3-Diaryl-3-oxopropylcarbamates by a Regiocontrolled Reduction of Ketoaziridines

Samimi

Yamin²,

Saberi

2014

Synthesis

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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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Oxidation and Reduction

Mehrotra

2007

Organic Reaction Mechanisms Series

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Selective reduction of α,β-epoxyketones to β-hydroxyketones using silyllithium reagents

Cited by 17 publications

References 35 publications

Synthesis of tert-Butyl 1,3-Diaryl-3-oxopropylcarbamates by a Regiocontrolled Reduction of Ketoaziridines

Synthesis of tert-Butyl 1,3-Diaryl-3-oxopropylcarbamates by a Regiocontrolled Reduction of Ketoaziridines

The Brook Rearrangement

Oxidation and Reduction

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