Electrophilic and nucleophilic organoselenium reagents.  New routes to .alpha.,.beta.-unsaturated carbonyl compounds

SHARPLESS, K. B.; Lauer, R. F.; Teranishi, A. Y.

doi:10.1021/ja00799a062

Cited by 493 publications

(148 citation statements)

References 5 publications

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“…Considering the obsewed difficulty in achieving dehydrobromination, we examined the popular and reliable selenylation -oxidative elimination approach previously used successfully (24) to prepare 2 in unreported yield. Keto ester 8 was treated with phenylselenenyl chloride and pyridine (3,25,26). The intermediate selenide was oxidized with hydrogen peroxide to give dienophile 2 in 95% overall yield from 8.…”

Section: Resultsmentioning

confidence: 99%

Diels–Alder reactions of 2-carbomethoxy-4,4-dimethyl-2-cyclopenten-1-one

Liu¹,

Ulíbarri²,

Browne³

1992

Can. J. Chem.

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Diels–Alder additions to keto ester 2 proceed in moderate to high yields with a variety of dienes under selected Lewis acid and thermal conditions. Thermal conditions provide the highest total yields for non-functionalized dienes, but Lewis acid catalysts, particularly stannic chloride, provide highly selective additions in greater net yields. A study of several functionalized dienes shows that zinc chloride is particularly effective in catalyzing additions to 2. No difference in stereoselectivity is observed between zinc chloride and thermal reactions for highly functionalized dienes. The significance of the regiochemical and stereochemical results of the Diels–Alder reactions is discussed.

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Section: Resultsmentioning

confidence: 99%

Diels–Alder reactions of 2-carbomethoxy-4,4-dimethyl-2-cyclopenten-1-one

Liu¹,

Ulíbarri²,

Browne³

1992

Can. J. Chem.

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“…With ester 15 in hand, the introduction of a double bond conjugated to the ester group via selenation-oxidative elimination (16) was attempted in light of the prospect that it would permit conjugate addition of the required methyl group. The maneuver proved unfruitful.…”

Section: Resultsmentioning

confidence: 99%

Diels–Alder approach to (±)-longifolene: A formal synthesis

Ho¹,

Yeh²,

Yule³

et al. 1992

Can. J. Chem.

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“…After purification, (S)-3-phenyl-2-(selenophenyl)propan-1-ol, 1 was isolated with an overall yield of 55%. 10,11 It is worth mentioning that the α-selenoalcohol is quite stable and can be stored at 10 °C for more than six months.…”

Section: Enantiomeric Excess Detection With (S)-mentioning

confidence: 99%

Enantiomeric excess detection with (S)-3-Phenyl-2-(selenophenyl)propan-1-ol derivatizing agent via mix and shake 77Se NMR

Ferreira¹,

Gonçalves²

2010

J. Braz. Chem. Soc.

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Neste artigo demonstramos que o composto (S)-3-fenil-2-(selenofenil)propan-1-ol pode ser empregado com sucesso como agente de derivatização quiral na determinação de excesso enantiomérico de substratos ácidos carboxílicos quirais via RMN de 77 Se. Os derivados diastereoméricos são obtidos através da mistura do agente de derivatização quiral com um substrato ácido não racêmico no próprio tubo de RMN e o excesso enantiomérico é determinado com apenas um espectro. Os melhores resultados foram os obtidos com o emprego do (S)-3-fenil-2-(selenofenil)propan-1-ol, que apresentou boas anisocronias para os sinais de selênio, variando entre Dd = 22 Hz a Dd = 211 Hz, mesmo com até 5 ligações separando o estereocentro do átomo de selênio.In this article, we demonstrate that (S)-3-phenyl-2-(selenophenyl)propan-1-ol can be successfully employed as chiral derivatizing agent for enantiomeric excess determination of chiral carboxylic acid substrates via 77 Se NMR. The required derivatives are obtained by mixing the chiral derivatizing agent with the non racemic carboxylic acid substrate directly in the NMR tube and determining the enantiomeric excess with just one spectrum. The best results were obtained with (S)-3-phenyl-2-(selenophenyl)propan-1-ol, which showed good anysochronies of the selenium signals, ranging from Dd = 22 Hz to Dd = 211 Hz, even with the stereocenter and the selenium atom five bonds apart.

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Electrophilic and nucleophilic organoselenium reagents. New routes to .alpha.,.beta.-unsaturated carbonyl compounds

Cited by 493 publications

References 5 publications

Diels–Alder reactions of 2-carbomethoxy-4,4-dimethyl-2-cyclopenten-1-one

Diels–Alder reactions of 2-carbomethoxy-4,4-dimethyl-2-cyclopenten-1-one

Diels–Alder approach to (±)-longifolene: A formal synthesis

Enantiomeric excess detection with (S)-3-Phenyl-2-(selenophenyl)propan-1-ol derivatizing agent via mix and shake 77Se NMR

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