Asymmetric Catalytic Borylation of α,β-Unsaturated Acceptors

Lee, Sumin; Yun, Jaesook

doi:10.1007/978-3-319-13054-5_3

Cited by 17 publications

(5 citation statements)

References 52 publications

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“…The products from these reactions are noteworthy. For example, although ample methods are available for the synthesis of β-carbonyl boronic esters (e.g., by conjugate addition to Michael acceptors), there are few examples for the synthesis of γ-carbonyl boronic esters that are now easily accessible using the current methodology. Furthermore, it is not possible to create compounds like 40 by existing metalate rearrangements since intermediate boronate complexes with β-leaving groups undergo elimination instead of 1,2-migration …”

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confidence: 99%

Merging Photoredox with 1,2-Metallate Rearrangements: The Photochemical Alkylation of Vinyl Boronate Complexes

2017

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Vinyl boronates react with electron-deficient alkyl iodides in the presence of visible light to give boronic esters in which two new C-C bonds have been created. The reaction occurs by radical addition of an electron-deficient alkyl radical to the vinyl boronate followed by electron transfer with another molecule of alkyl iodide, continuing the chain, and triggering a 1,2-metalate rearrangement. In a number of cases, the use of a photoredox catalyst enhances yields significantly. The scope of the radical precursor includes α-iodo ketones, esters, nitriles, primary amides, α-fluorinated halo-acetates and perfluoroalkyl iodides.

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confidence: 99%

Merging Photoredox with 1,2-Metallate Rearrangements: The Photochemical Alkylation of Vinyl Boronate Complexes

2017

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“…As organoboranes are valuable reagents in organic synthesis due to their versatility in functionalization, the demand for stereochemically well-defined organoboronates is increasing . While useful methods to prepare enantioenriched organoboron compounds have been developed, such as metal-catalyzed borylation and stoichiometric lithiation–borylation, the search for novel and more powerful asymmetric synthetic methods continues. In general, the creation of simple alkylboron compounds with high enantiocontrol presents a greater challenge than the production of boron compounds with a biasing or directing substituent …”

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confidence: 99%

Asymmetric Synthesis of Borylalkanes via Copper-Catalyzed Enantioselective Hydroallylation

et al. 2016

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An efficient synthetic method for preparing enantioenriched secondary borylalkanes has been achieved through a copper-catalyzed regio- and enantioselective hydroallylation of alkenyl boronates and boramides employing hydrosilanes and allylic phosphates. In the presence of a copper catalyst with a chiral Walphos ligand, a range of alkenylboron compounds with an aryl, heteroaryl, or alkyl substituent produced secondary homoallylic alkylboron compounds in good yields and with high enantioselectivities up to 99% ee. The utility of the resulting alkylboronates was demonstrated in an efficient synthesis of (S)-massoialactone.

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“…Organoboron compounds are important synthetic intermediates, and the carbonyl group is one of the most ubiquitous and important functional groups in organic chemistry. Chiral β-borylated carbonyl compounds containing both boron and carbonyl groups are potentially versatile intermediates in organic synthesis and their preparation has attracted much attention . Methods for the straightforward synthesis of these compounds are limited to the asymmetric borylation of α,β-unsaturated carbonyl compounds, which involves conjugate addition of a nucleophilic boron species to the β-carbon of the enone (Scheme A).…”

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confidence: 99%

Copper-Catalyzed Asymmetric Borylacylation of Styrene and Indene Derivatives

Yang

Lü

et al. 2021

J. Org. Chem.

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The enantioselective copper-catalyzed borylacylation of aryl olefins with acyl chlorides and bis-(pinacolato)diboron is reported. This three-component reaction involves an enantioselective syn-borylcupration of the aryl olefin, followed by a nucleophilic attack on the acyl chloride. This reaction proceeds with a 2 mol % catalyst loading and is generally completed within 30 min at room temperature. Because the boron moiety can be converted into versatile functional groups and the carbonyl group is a ubiquitous functional group, the resulting chiral β-borylated ketones are versatile intermediates in organic synthesis.

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Asymmetric Catalytic Borylation of α,β-Unsaturated Acceptors

Cited by 17 publications

References 52 publications

Merging Photoredox with 1,2-Metallate Rearrangements: The Photochemical Alkylation of Vinyl Boronate Complexes

Merging Photoredox with 1,2-Metallate Rearrangements: The Photochemical Alkylation of Vinyl Boronate Complexes

Asymmetric Synthesis of Borylalkanes via Copper-Catalyzed Enantioselective Hydroallylation

Copper-Catalyzed Asymmetric Borylacylation of Styrene and Indene Derivatives

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