Pyrolyse des N-oxydes des trans-pyrrolidino-2 cyclohexanols

Gore, J.; Drouet, J.P.; Barieux, J.-J.

doi:10.1016/s0040-4039(01)97638-5

Cited by 7 publications

(5 citation statements)

References 6 publications

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“…Alkyl-substituted amino alcohols 16 can possible to convert symmetrically substituted cyclohexanones to the asymmetrically substituted compound 17 via β-aminoalkylborane 15 (Scheme 6) [11][12][13].…”

Section: Methodsmentioning

confidence: 99%

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Boranes in Organic Chemistry 2. β-Aminoalkyl- and β-sulfanylalkylboranes in organic synthesis

Dembitsky

Толстиков

Srebnik

2017

Eurasian Chem. Tech. J.

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Problems on using of β-aminoalkyl- and β-sulfanylalkylboranes in organic synthesis are considered in this review. The synthesis of boron containing a-aminoacids by Curtius rearrangement draws attention. The use of β-aminoalkylboranes available by enamine hydroboration are described. Examples of enamine desamination with the formation of alkenes, aminoalcohols and their transformations into allylic alcohol are presented. These conversions have been carried out on steroids and nitrogen containing heterocyclic compounds. The dihydroboration of N-vinyl-carbamate and N-vinyl-urea have been described. Examples using nitrogen and oxygen containing boron derivatives for introduction of boron functions were presented. The route to borylhydrazones by hydroboration of enehydrazones was envisaged. The possibility of trialkylamine hydroboration was shown on indole alkaloids and 11-azatricyclo-[6.2.11,802,7]2,4,6,9-undecatetraene examples. The synthesis of β-sulfanyl-alkylboranes by various routes was described. The synthesis of boronic thioaminoacids was carried out by free radical thiilation of dialkyl-vinylboronates. Ethoxyacetylene has been shown smoothly added 1-ethylthioboracyclopentane. Derivatives of 1,4-thiaborinane were readily obtained by divinylboronate hydroboration. Dialkylvinylboronates react with mercaptoethanol with the formation of 1,5,2-oxathioborepane derivatives. Stereochemistry of thiavinyl esters hydroboration leading to stereoisomeric β-sulfanylalkylboranes are discussed. Examples of radical thiilation of various structural types vinylboronates were presented. In particular, 1,3,2-dioxaborinanes and 1,3,2-dioxaborolanes, containing by boron atom vinyl-, propenyl-, isopropenylor isopropylidene substituents have been used. Thiilation has been achieved by use of alkylmercaptanes, as well as mercaptamine derivatives. Alkylmercaptanes were able to replace the bromine substituent in tris-(2-bromoctyl)-borane. Dialkylvinylborates have been added hydrosulfite with the formation of 2-boronoethane sulfuric acids. A lot of examples of radical thiilation of vinylboronic acid dialkyl esters with mercaptoacids are presented. Under the azaisobutyric acid dinitryle conditions thioglycolic, β-mercaptopropionic, 2-mercaptoamberic acids and their esters as well as cysteine were added. Vinyl-, propenyl- and isopropenyldioxaborolanes were also participated in the thiilation with the formation of acetic, propionic or amberic acid thioethanoboronates. The high reactivity of B,B,B-trivinyl-N,N,N-triphenylborazine in the reaction with thiophenol, leading to B-tris-(phenylmercaptoethyl)-N-phenylborazine was shown. The problems of asymmetric hydroboration leading to chiral β-sulfanylalkylboranes were discussed briefly. In particular, an example, including dihydro-thiophene hydroboration, leading to (+)-R-thiofan-3-yl-diisopinocamphenylborane, and the interaction with acetaldehyde with the formation of (+)-R-3-thiophanyl-diethoxyborane was implemented. The reaction with 3,4-dihydrothiapyrane proceeds analogously. A synthetic route to sulfono-norbornen-boronic acid esters by Diels-Alder reaction of cyclopentadiene with arylsulfanyl-vinylboronic acid esters has been discussed.

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Section: Methodsmentioning

confidence: 99%

“…A keto group in an adjacent position could also be obtained on a series of asymmetrically substituted cyclic ketones via β-aminoalkylborane 18 (Scheme 7) [11,13].…”

Section: Methodsmentioning

confidence: 99%

Boranes in Organic Chemistry 2. β-Aminoalkyl- and β-sulfanylalkylboranes in organic synthesis

Dembitsky

Толстиков

Srebnik

2017

Eurasian Chem. Tech. J.

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“…(8) In 1970, Gore and Barieux 7 reported, in the first of a series of six papers, that the hydroboration of the pyrrolidine enamine of dihydrotestosterone 17 with diborane in THF followed by treatment of the intermediate organoborane with refluxing methanol afforded an 80-85% yield of an 82:18 mixture of the isomeric aminosteroids 18a and 18b (Equation 9). (9) In the following year, Barieux and Gore reported a 1,2-carbonyl transposition sequence in which the hydroboration/oxidation of an enamine to the corresponding trans-2-aminoalcohol was a key step (Equation 10).…”

Section: (5)mentioning

confidence: 99%

“…(9) In the following year, Barieux and Gore reported a 1,2-carbonyl transposition sequence in which the hydroboration/oxidation of an enamine to the corresponding trans-2-aminoalcohol was a key step (Equation 10). [8][9][10] (10)…”

Section: (5)mentioning

confidence: 99%

The hydroboration of enamines

Goralski¹,

Singaram²

2012

Arkivoc

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This review describes the hydroboration of enamines in chronological order covering early work to give β-amino alcohols and reduction products and then our more recent work to give β-aminoorganoboranes and their subsequent conversion into β-amino alcohols, β-aminoboronic esters and acids, and olefins. Analytical methods to determine the enantiomeric excess (ee) of the β-amino alcohols obtained from the asymmetric hydroboration of enamines are also described.

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“…α,β-Unsaturated ketones are ubiquitous and useful compounds whose synthesis and reactions have been actively investigated . Their synthesis by boron-related chemistry includes hydroboration/oxidation of enamines followed by N -oxide decomposition and oxidation of the allylic alcohols, hydroboration of 1-halo alkynes with thexylborane followed by coupling and oxidation, oxidation of 1,2-oxaboracyclopent-4-enes, intramolecular transfer reactions with α-halo-α-carbonyl carbanions, by palladium-catalyzed coupling of 1-alkenylboronates with haloenones or palladium-induced coupling of α-iodoenones with 9-alkyl-9-BBN, and carbonylative cross-coupling . We have very recently prepared a series of 1,3-dibora-1,3-butadienes by zirconocene-mediated reductive cyclization of 1-alkynyl boronates (eq 1) …”

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confidence: 99%