.alpha.-Halo boronic esters: intermediates for stereodirected synthesis

Matteson, Donald S.

doi:10.1021/cr00097a009

Cited by 391 publications

(157 citation statements)

References 68 publications

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“…An optically active boron analogue of phenylalanine has been obtained using the α-haloboronic ester 29 [20]. The use of (+)-pinanediol for boronic acid protection allowed the preparation of an optically pure of 30 (Scheme 7).…”

Section: Synthesis Of Optically Active Analogue Of Phenylalaninementioning

confidence: 99%

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%

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

2016

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“…[3]). 36) In the revised synthesis, they successfully exploited Matteson's asymmetric homologation [37][38][39] to introduce contiguous stereocenters, using (þ)-and (À)-pinanediol as chiral directors. Chiral boronate 26 obtained from (þ)-pinanediol was subjected to asymmetric homologation to insert the first stereocenter to give -chloro derivative.…”

Section: Other Syntheses Of Microcarpalide Employing Rcmmentioning

confidence: 99%

Synthetic Studies of Natural 10-Membered Lactones, Mueggelone, Microcarpalide, and Sch 642305, Which Have Interesting Bioactivities

Ishigami

2009

Bioscience, Biotechnology, and Biochemistry

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A number of 10-membered lactones have been isolated as secondary metabolites, and many of them have interesting and potent activities. Because of synthetic and biological interests, many synthetic studies of these compounds have been made. This review summarizes synthetic approaches to three natural 10-membered lactones, mueggelone, microcarpalide, and Sch 642305. Mueggelone is an inhibitor of fish development, microcarpalide is a microfilament disrupting agent, and Sch 642305 is an inhibitor of bacterial DNA primase.

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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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.alpha.-Halo boronic esters: intermediates for stereodirected synthesis

Cited by 391 publications

References 68 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

Synthetic Studies of Natural 10-Membered Lactones, Mueggelone, Microcarpalide, and Sch 642305, Which Have Interesting Bioactivities

New Asymmetric Syntheses with Boronic Esters and Fluoroboranes

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