Exploratory study on photoinduced single electron transfer reactions of .alpha.,.beta.-epoxy ketones with amines

Hasegawa, Eietsu; Ishiyama, Kenyuki; Horaguchi, Takaaki; Shimizu, Takahachi

doi:10.1021/jo00004a052

Cited by 85 publications

(32 citation statements)

References 1 publication

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“…The pure product was obtained by chromatography on silica gel (200-300 mesh) eluted with petroleum ether or a mixture of petroleum ether and acetone. The authenticity was established by comparing their melting points with literature 10,12…”

Section: Methodsmentioning

confidence: 99%

An efficient and practical synthesis of β-hydroxyl ketones catalysed by trisodium phosphate under ultrasound

Chen

et al. 2004

Journal of Chemical Research

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The aldol condensation is one of the most important carboncarbon bond-forming reactions in organic chemistry. 1 Over the past several years, research in the area of aldol type addition reactions has dramatically increased. This is due, in part, to the large number of important natural products containing the β-hydroxyl carbonyl unit.Aldol reaction have been classically conducted in the presence of a strong base or acid. 2 However, under such conditions, the synthesis of the desired aldol product is plagued by the formation of the concomitant α,β-unaturated ketone, Michael addition to the formed enone, and so on. To overcome these problems, various Lewis acids 3 or bases 4 have been employed as alternative catalysts, but in most cases the ketones need to be modified as silyl enol ethers, ketene silyl acetals, etc. Meanwhile, aldol reactions can also be carried out in the presence of phase-transfer catalysts such as TBAF 5 and calix [6] arene derivatives 6 or without catalyst 7 , but the ketones also need to be modified. In recent years, proline-catalysed aldol reactions in aqueous micelles have been reported. 8 In addition, potassium phosphate was found to catalyse the condensation of nitroalkanes with various aliphatic and aromatic aldehydes to form nitroaldols. Most recently, Na 2 CO 3 has been used to promote aldol reactions of unmodified ketones with reactive aldehydes in pure water. 10 However, in spite of their potential utility, some of the reported methods suffer from drawbacks such as longer reaction times and lower yields.

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Section: Methodsmentioning

confidence: 99%

An efficient and practical synthesis of β-hydroxyl ketones catalysed by trisodium phosphate under ultrasound

Chen

et al. 2004

Journal of Chemical Research

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“…The NMR-spectrum of the product was in accordance with published data. 48 Non-aqueous solution phase aldol reactions 2-[Trimethylsilyloxy(4-methoxyphenyl)methyl]cyclohexanone 7c. 4-Hydroxybenzaldehyde (121 mm 3 , 1 mmol) and 1-(trimethylsilyloxy)cyclohexene (211 mm 3 , 1.1 mmol) were dissolved in THF (1 cm 3 ) and added to a stirred suspension of Y(OTf) 3 in DCM (1.5 cm 3 ) at 0 ЊC.…”

Section: -Hydroxy-3-(4-methoxyphenyl)-1-phenylpropan-1-onementioning

confidence: 99%

Towards peptide isostere libraries: aqueous aldol reactions on hydrophilic solid supports

Graven

Grötli

Meldal

2000

J. Chem. Soc., Perkin Trans. 1

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“…This reaction was performed as described above by changing the addition of lithium dicyclohexylamide to a mixture of indium trichloride, 5 and benzaldehyde. 2,3-Epoxy-1,3diphenylpropan-1-one ( 7) 16 (258 mg, 77%, trans 100%) was obtained.…”

Section: The Cross-coupling Reaction Of 5 With Benzaldehyde [Eqn (4)]mentioning

confidence: 99%

A facile preparation of indium enolates and their Reformatsky- and Darzens-type reactions

Hirashita

Kinoshita

Yamamura

et al. 2000

J. Chem. Soc., Perkin Trans. 1

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Exploratory study on photoinduced single electron transfer reactions of .alpha.,.beta.-epoxy ketones with amines

Cited by 85 publications

References 1 publication

An efficient and practical synthesis of β-hydroxyl ketones catalysed by trisodium phosphate under ultrasound

An efficient and practical synthesis of β-hydroxyl ketones catalysed by trisodium phosphate under ultrasound

Towards peptide isostere libraries: aqueous aldol reactions on hydrophilic solid supports

A facile preparation of indium enolates and their Reformatsky- and Darzens-type reactions

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