α-Halo boronic esters in asymmetric synthesis

Matteson, Donald S.

doi:10.1016/s0040-4020(98)00321-4

Cited by 229 publications

(106 citation statements)

References 110 publications

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“…In some cases, the synthesis of α-haloalkylboranes was accompanied by β-haloalkylboranes. Conditions and/or reactants for the formation of α-,β-boryl alkyl halides differ from those used for obtaining α-boryl alkyl halides [1,2,5,6,8].…”

Section: Synthesis Of Optically Active Analogue Of Phenylalaninementioning

confidence: 99%

“…The organoboranes obtained from tetraalkyldiboranes and/or allyl chlorides react with aqueous alkali, or metal hydrides and form cyclopropane rings 143 with different alkyl fragments (X = halides) according to following general reaction (Scheme 49) [5,6,41]. …”

Section: Reactions With Allyl Chloridesmentioning

confidence: 99%

“…α-, β-, γ-Haloalkylboranes are rare groups of synthetic compounds with common structures such as B-C-X, B-C-C-X, B-C-C-C-X (X = F, Cl, Br or I) are mainly intermediate compounds in hydroboration reactions partly given in some reviews [1][2][3][4][5][6][7][8][9]. …”

Section: Introductionmentioning

confidence: 99%

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Boranes in Organic Chemistry 3. α-, β- and γ-Haloalkylboranes: The Perspective Vehicles for Organic Synthesis

2016

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<p>The methods of synthesis of α− and β−haloalkylboranes, including chloration of alkylboronic acid esters, additive bromation and chloration of esters of vinyl- and alkenylboronic acids, addition of bromine to trivinylborazines have been considered. The reactions of radical addition of polyhaloidmethanes to vinylboranes, α− and β−unsaturated boronic esters, B-vinyl-B-arylboronic esters, B-trivinyl-B-triarylborazines were discussed. The hydroboration of acetylenic halogenides of dicycloalkylboranes, which led to halocontaining derivatives of dialkylvinylborane was separately considered. The examples of hydroboration of halogenides of allyl and vinyl types are presented. The reaction of dienic synthesis, which takes place between vinylchloroboranes or vinylboronic esters and tetra- or hexachlorocyclopentadienes has been discussed. The reaction of alkenes and allenes with boron tribromide was described. The Markovnikov and non-Markovnikov hydrobromation of boron vinylderivatives has been envisaged. The approaches to the synthesis of perfluoroalkylboranes on the base of hydroboration of perfluoroalkenes have been discussed. The methods of the synthesis of boronates, containing halogetaryl substituents, have been performed. The reactions of hydroboration of halogenides of allylic and propargylic types by 9-borabicyclononane have been shown. The regio- and stereoselectivity of the reaction has been discussed. The examples of the synthesis of boranes of the norbornene type were presented. The reaction of boroallylilation of allyl- and propargylhalogenides leading to the derivatives of 3-bora-bicyclo[3,3,1]-nonane has been discussed. Some directions of using of haloidalkylboranes in the synthesis have been discussed. The examples of nucleophilic substitution leading to oxyalkyl- and azidoalkylboranes have been presented. The route of obtaining of alcohols from α−haloidalkylboranes has been shown. The general scheme of synthesis of α−aminoboronic acids was perfomed. The general approach to the synthesis of allenes on the base of hydroboration products of propargyl halogenides has been discussed. The schemes of synthesis of 1,4-disubstituted-1,2,3-butatrienes are presented. The wide using reaction of introducing of vinylic group into substituent, bonding with boron atom in molecules of dialkylvinylboranes, was discussed. The reactions of new C-C bonds formation, based on the action of iodine on the alkylvinylboronates leading to 1,3-dienes and alkylidencyclanes have been shown. Τhe route of the synthesis of cyclopropanes from β−haloidalkylboranes has been discussed.</p>

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Section: Synthesis Of Optically Active Analogue Of Phenylalaninementioning

confidence: 99%

Section: Reactions With Allyl Chloridesmentioning

confidence: 99%

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Boranes in Organic Chemistry 3. α-, β- and γ-Haloalkylboranes: The Perspective Vehicles for Organic Synthesis

2016

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“…the dicyclohexyl boronate 18 obtained from Matteson's elegant methodology [41], lends access to α-alkyl substituted allylboronates (e.g., 19) with very high diastereomeric purity by way of a net inversion of configuration (Equation 9) [42]. Likewise, alkenylmetal fragments react with chiral dichloromethylboronate 20 to afford optically pure α-chloroallylboronates such as 21 (Equation 10) [43].…”

Section: Preparation Of Allylboronates and Their Use In Tandem Reactimentioning

confidence: 99%

Recent Advances in the Preparation of Allylboronates and Their Use in Tandem Reactions with Carbonyl Compounds

Kennedy

Hall

2005

Boronic Acids

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“…The reaction of (dichloromethyl)lithium with boronic esters of chiral diols (1) followed by zinc chloride-catalyzed rearrangement of the resulting (dichloromethyl)borate complex (2) leads to asymmetric (α-chloroalkyl)boronic esters (3) with diastereoselection often ~100:1 at the newly formed stereogenic α-carbon, as illustrated in Scheme 1 [1][2][3][4]. Reactions of 3 with a wide variety of nucleophiles (Y -) lead to various asymmetric boronic ester products 4.…”

Section: Introductionmentioning

confidence: 99%

New Asymmetric Syntheses with Boronic Esters and Fluoroboranes

Matteson

2004

ChemInform

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Efficient cleavage of sterically hindered boronic esters of asymmetric diols to recover both the diol and a more reactive borane derivative has been a challenging problem. A remarkable borosilicate glass-catalyzed cleavage with thionyl chloride and imidazole proved less useful than hoped for. Potassium bifluoride converts boronic esters to diols and alkyltrifluoroborates. These with chlorosilanes yield alkyldifluoroboranes, which with alkyl azides form secondary amines in high enantiopurity.

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α-Halo boronic esters in asymmetric synthesis

Cited by 229 publications

References 110 publications

Boranes in Organic Chemistry 3. α-, β- and γ-Haloalkylboranes: The Perspective Vehicles for Organic Synthesis

Boranes in Organic Chemistry 3. α-, β- and γ-Haloalkylboranes: The Perspective Vehicles for Organic Synthesis

Recent Advances in the Preparation of Allylboronates and Their Use in Tandem Reactions with Carbonyl Compounds

New Asymmetric Syntheses with Boronic Esters and Fluoroboranes

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