A Rapid Synthesis of 2-Aryl Polyhydroxylated Pyrrolidines

Su, Jiakun; Jia, Yue‐Mei; He, Ruirui; Rui, Peixin; Han, Narenchaoketu; He, Xihui; Xiang, Junfeng; Chen, Xin; Zhu, Jinghua; Yu, Chu-Yi

doi:10.1055/s-0029-1258085

Cited by 5 publications

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“…Unpolar solvents were not suitable for the hydrogenolysis, probably due to the low solubility and conversion of the fairly polar starting materials or intermediates. After these problems we tried to diminish the nucleophilicity of the amino group by addition of acid since this protocol has proved to be advantageous in other reduction processes of amines [54]. Acetic acid in methanol (1:5) was a good medium for our reductions and substrate 14 was now smoothly reduced under hydrogen atmosphere with palladium on charcoal.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of new enantiopure poly(hydroxy)aminooxepanes as building blocks for multivalent carbohydrate mimetics

Bouché¹,

Kandziora²,

Reißig³

2014

Beilstein J. Org. Chem.

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SummaryNew compounds with carbohydrate-similar structure (carbohydrate mimetics) are presented in this article. Starting from enantiopure nitrones and lithiated TMSE-allene we prepared three 1,2-oxazine derivatives which underwent a highly stereoselective Lewis acid-induced rearrangement to give bicyclic products in good yield. Subsequent reductive transformations delivered a library of new poly(hydroxy)aminooxepane derivatives. The crucial final palladium-catalyzed hydrogenolysis of the 1,2-oxazine moiety was optimized resulting in a reasonably efficient approach to a series of new seven-membered carbohydrate mimetics.

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Section: Resultsmentioning

confidence: 99%

Synthesis of new enantiopure poly(hydroxy)aminooxepanes as building blocks for multivalent carbohydrate mimetics

Bouché¹,

Kandziora²,

Reißig³

2014

Beilstein J. Org. Chem.

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Synthesis and Transformations of Nitrones for Organic Synthesis

2019

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Nitrones are important compounds and are highly useful in many aspects. The first part describes the methods for synthesis of nitrones, which are useful and environmentally friendly. Catalytic oxidations, condensations, and other useful reactions are described. The nitrones thus obtained are key intermediates for the synthesis of biologically important nitrogen compounds. The second part describes the fundamental transformations of nitrones, which will provide the strategies and means for the construction of nitrogen compounds. The reactions with nucleophiles or radicals, C–H functionalization, and various addition reactions are described. The last reactions are particularly important for highly selective carboncarbon bond formations. 1,3-Dipolar cycloaddition reactions are excluded because the size of the review is limited and excellent reviews have been published in Chemical Reviews.

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Oxaazabicyclooctene Oxides, Another Type of Bridgehead Nitrones: Diastereoselective Assembly from Acetylene Gas, Ketones, and Hydroxyl Amine

et al. 2020

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Unique bridgehead nitrones, 8-oxa-6-azabicyclo[3.2.1]oct-6-ene 6-oxides, have been assembled diastereoselectively via acetyldihydropyrans, products of one-pot self-organization of two molecules of ketones and two molecules of acetylene, which after oximation undergo acid-catalyzed ring closure. The proposed mechanism includes the enol double-bond protonation, followed by intramolecular cyclization involving the interaction of the carbocation formed with a nitrogen atom. A broad range of substrates tolerate this facile transformation, in which the bridgehead nitrones were isolated in high yields.

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A Rapid Synthesis of 2-Aryl Polyhydroxylated Pyrrolidines

Cited by 5 publications

References 0 publications

Synthesis of new enantiopure poly(hydroxy)aminooxepanes as building blocks for multivalent carbohydrate mimetics

Synthesis of new enantiopure poly(hydroxy)aminooxepanes as building blocks for multivalent carbohydrate mimetics

Synthesis and Transformations of Nitrones for Organic Synthesis

Oxaazabicyclooctene Oxides, Another Type of Bridgehead Nitrones: Diastereoselective Assembly from Acetylene Gas, Ketones, and Hydroxyl Amine

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