Sugar amide-pyrrolidine catalyst for the asymmetric Michael addition of ketones to nitroolefins

Kumar, Togapur Pavan; Balaji, Sirinyam Venugopal

doi:10.1016/j.tetasy.2014.02.003

Cited by 27 publications

(10 citation statements)

References 98 publications

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“…Other sugar-pyrrolidine organocatalysts for the Michael addition were prepared in 2014 by Kumar and Balaji [ 162 ] starting from the d -xyluronic acid derivatives 355 and 358 ( Scheme 96 ). The d -glucofuranose diacetonide 75 was first converted [ 163 ] into the epimer 223 by oxidation with pyridinium chlorochromate (PCC) and hydride reduction, and then triflation of 223 and a reaction with sodium azide afforded the 3-azido- d -glucofuranose 354 as described [ 163 ].…”

Section: Variously Functionalized Carbohydratesmentioning

confidence: 99%

“…Regioselective acid hydrolysis of the latter and oxidation of the resulting diol afforded the acid 355 ; however, the reaction conditions, yield and analytical data were not reported [ 164 ]. The azido-acid was coupled [ 162 ] with the amine 356 to give, after catalytic hydrogenation, the organocatalyst 357 . Unfortunately, the synthesis and analytical data of the proline-derived amine 356 were not provided [ 162 ].…”

Section: Variously Functionalized Carbohydratesmentioning

confidence: 99%

“…The azido-acid was coupled [ 162 ] with the amine 356 to give, after catalytic hydrogenation, the organocatalyst 357 . Unfortunately, the synthesis and analytical data of the proline-derived amine 356 were not provided [ 162 ]. The organocatalyst 359 was prepared in a similar way, but the synthesis and analytical data (or a correct bibliographic reference) of the acid 358 were missing [ 162 ].…”

Section: Variously Functionalized Carbohydratesmentioning

confidence: 99%

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Synthesis and Applications of Carbohydrate-Based Organocatalysts

et al. 2021

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Organocatalysis is a very useful tool for the asymmetric synthesis of biologically or pharmacologically active compounds because it avoids the use of noxious metals, which are difficult to eliminate from the target products. Moreover, in many cases, the organocatalysed reactions can be performed in benign solvents and do not require anhydrous conditions. It is well-known that most of the above-mentioned reactions are promoted by a simple aminoacid, l-proline, or, to a lesser extent, by the more complex cinchona alkaloids. However, during the past three decades, other enantiopure natural compounds, the carbohydrates, have been employed as organocatalysts. In the present exhaustive review, the detailed preparation of all the sugar-based organocatalysts as well as their catalytic properties are described.

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Section: Variously Functionalized Carbohydratesmentioning

confidence: 99%

Section: Variously Functionalized Carbohydratesmentioning

confidence: 99%

Section: Variously Functionalized Carbohydratesmentioning

confidence: 99%

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Synthesis and Applications of Carbohydrate-Based Organocatalysts

et al. 2021

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“…Several β-nitrostyrenes were used as electrophiles in the reaction with cyclohexanone, providing good results irrespective of the nature of substitution at the aromatic ring. Also cyclopentanone and acetone were suitable pro-nucleophiles, although the achieved results, in terms of yields and selectivities, were lower compared to those obtained with standard cyclohexanone [ 83 ].…”

Section: Carbon Nucleophilesmentioning

confidence: 99%

Recent Advances in Asymmetric Organocatalyzed Conjugate Additions to Nitroalkenes

et al. 2017

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The asymmetric conjugate addition of carbon and heteroatom nucleophiles to nitroalkenes is a very interesting tool for the construction of highly functionalized synthetic building blocks. Thanks to the rapid development of asymmetric organocatalysis, significant progress has been made during the last years in achieving efficiently this process, concerning chiral organocatalysts, substrates and reaction conditions. This review surveys the advances in asymmetric organocatalytic conjugate addition reactions to α,β-unsaturated nitroalkenes developed between 2013 and early 2017.

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“…In the absence of solvent the reaction was also significantly faster (Scheme ). The performance of a sugar amide/pyrrolidine catalyst featuring the furanose form of the carbohydrate was also tested in this reaction by Kumar and Balaji 15. With cyclic ketones similar yields but higher diastereoselectivities could be obtained, also under solvent‐free conditions.…”

Section: Carbohydrate‐based Prolinamidesmentioning

confidence: 99%

Applications of Carbohydrate‐Based Organocatalysts in Enantioselective Synthesis

Phillips

2014

Eur J Org Chem

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Carbohydrates have been widely used for stereochemical control, either as chiral auxiliaries or as ligands. Their natural abundance and rigidity of structure, together with the presence of many functional groups, have also in recent years made them attractive chiral modular units for the assembly of bifunctional organocatalysts. Applications have ranged from the more complex bifunctional carbohydrate‐based amine–(thio)ureas and prolinamides to simple amino alcohols. The presence of many hydroxy groups and their consequent water solubility has allowed for the study of reactions in aqueous media. Nowadays they have been applied to many reactions such as the aldol, Michael, Stetter, Biginelli, Morita–Baylis–Hillman, decarboxylative Mannich and other reactions, and even to the multistep synthesis of known drugs. This review provides an overview of developments in this field in the period from 2009 to mid‐2014.

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Sugar amide-pyrrolidine catalyst for the asymmetric Michael addition of ketones to nitroolefins

Cited by 27 publications

References 98 publications

Synthesis and Applications of Carbohydrate-Based Organocatalysts

Synthesis and Applications of Carbohydrate-Based Organocatalysts

Recent Advances in Asymmetric Organocatalyzed Conjugate Additions to Nitroalkenes

Applications of Carbohydrate‐Based Organocatalysts in Enantioselective Synthesis

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