Enantiomerically pure pyruvate derivatives by epoxidation of ylidenediketopiperazines

Bartels, A.; Jones, Peter G.; Liebscher, Jürgen

doi:10.1016/0040-4039(95)00600-h

Cited by 19 publications

(10 citation statements)

References 7 publications

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“…Scheme 4 Dimethyldioxirane [19,20] has become a reliable reagent in epoxidation of N-acylenamine moieties. [21][22][23][24] Its reaction with dihydroimidazo[2,1-a]isoquinolines 5 was highly stereoselective (dr Ͼ 95:5) affording excellent yields of the oxiranes 8a,b (see Scheme 2). MCPBA was successfully applied in the epoxidation of an anthraquinone-derived acylenamine.…”

Section: Resultsmentioning

confidence: 99%

Asymmetric Synthesis of Isoquinoline Derivatives from Amino Acids

2005

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Reaction of isoquinolines 1 with N-arylsulfonylamino acid fluorides 2 provides a highly stereoselective access to new dihydroimidazo[2,1-a]isoquinolin-3-ones 5 via intermediate N-acylisoquinolinium salts 3. Addition reactions to the enamine double bond, such as hydrogenation or epoxidation with dimethyldioxirane, leads to tetrahydroimidazo[2,1-a]isoquinoline-3-ones 6, 7 and oxiranes 8, respectively. Opening of the oxirane ring of the 8 with nucleophiles allows the synthesis of hydroxytetrahydroimidazo[2,1-a]isoquinolin-3-ones

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Section: Resultsmentioning

confidence: 99%

Asymmetric Synthesis of Isoquinoline Derivatives from Amino Acids

2005

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“…The stereochemical mode of formation of epoxides 2 was proved by X-ray crystal analysis of compound 2c. 2 All compounds 2 exhibit the same sign of optical rotation ( Table 2). The configuration at the hemiaminal carbon atom of diols 3 remains unknown.…”

mentioning

confidence: 94%

“…Our preliminary investigations into the possibility of epoxidation of 3-ylidenepyrazine-2,5-diones 1 revealed that the powerful reagent dimethyldioxirane allowed the synthesis of the corresponding spirooxiranes 2, which represent configurationally stable a-keto acid derivatives. 2 Full experimental details, investigation of alternative routes and some reactions of the spirooxiranes 2 are reported in the present paper.…”

mentioning

confidence: 99%

Stereoselective Epoxidation and Bromoalkoxylation with 3-Ylidenepyrazine-2,5-diones

Bartels¹,

Jones²,

Liebscher³

2003

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3-Ylidenepyrazine-2,5-diones 1 were stereoselectively epoxidsed by dimethyldioxirane giving access to spirooxiranes 2 and diols 3. Bromohydroxylation and bromoalkoxylation of 3ylidenepyrazine-2,5-diones 1 produced high yields of optically active 3-(1-bromoalkyl)pyrazine-2,5-diones 4 with a 3-hydroxy or 3alkoxy function, respectively. Whereas direct hydrogenation of epoxides 2 afforded epimeric mixtures of 3-(1-hydroxyalkyl)pyrazine-2,5-diones 5 and 6, the highly stereoselective transformation into 5 was possible by primary acid cleavage of the oxirane ring followed by hydrogenation of the resulting keto-enol mixtures 7/8.

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“…Sonogashira 偶联反应 [15] ; Suzuki 偶联反应 [16] ; 复分解反应 [17] ; 环加成反应 [18] ; 环氧化反应 [19,20] ; 氢化反应 [21～23] 和迈克尔加成反应 [24～26] 等. 因此有关 α,β-脱氢氨类化合物(功能化烯胺)的合成方法长期以来已成为有机界关注的热点之一.…”

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