Novel synthesis of carbohydrate-derived organocatalysts and their application in asymmetric aldol reactions

Shen, Chao; Liao, Hanxiao; Shen, Fangyi; Zhang, Pengfei

doi:10.1016/j.catcom.2013.07.011

Cited by 16 publications

(13 citation statements)

References 29 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In 2013, Zhang and co-workers described [ 151 ] the preparation of the fully O -protected sugar prolinamide 310 and its free-OH derivative 311 ( Scheme 85 ) from the known pivaloated glucosylamine 309 . Regrettably, the synthesis of the latter from the penta- O -pivaloyl d -glucopyranose 307 was not reported in the article [ 151 ] and the bibliographic references quoted therein did not deal with the preparation and analytical data of sugars 307–309 .…”

Section: Sugar Prolinamidesmentioning

confidence: 99%

Synthesis and Applications of Carbohydrate-Based Organocatalysts

et al. 2021

View full text Add to dashboard Cite

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.

show abstract

Section: Sugar Prolinamidesmentioning

confidence: 99%

Synthesis and Applications of Carbohydrate-Based Organocatalysts

et al. 2021

View full text Add to dashboard Cite

show abstract

“…During the past two decades, significant efforts have been devoted to developing efficient scaffolds for the construction of chiral organocatalysts [43]. The vast majority of organocatalysts are amine compounds [44], which are usually chiral structures that comprise various organic moieties, such as chiral amino alcohols, diamines, prolinamides, and their derivatives.…”

Section: Microbial Reduction Of Prochiral Ketonesmentioning

confidence: 99%

Selection of microbial biocatalysts for the reduction of cyclic and heterocyclic ketones

Bianchi

Varela

Bianchi

et al. 2017

Process Biochemistry

View full text Add to dashboard Cite

show abstract

“…Cross‐aldol reactions between butanone and aryl aldehydes provided the required products with high yields and selectivities (Table 2); interestingly, the reactions took place exclusively at the 3‐position of the ketone. One year later the same group reported a new catalyst with all hydroxyl groups protected by pivaloyl groups, which was also very efficient 13. It worked better in DMSO/water than in water alone, but also in the presence of benzoic acid as co‐catalyst.…”

Section: Carbohydrate‐based Prolinamidesmentioning

confidence: 99%

Applications of Carbohydrate‐Based Organocatalysts in Enantioselective Synthesis

Phillips

2014

Eur J Org Chem

View full text Add to dashboard Cite

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.

show abstract

Novel synthesis of carbohydrate-derived organocatalysts and their application in asymmetric aldol reactions

Cited by 16 publications

References 29 publications

Synthesis and Applications of Carbohydrate-Based Organocatalysts

Synthesis and Applications of Carbohydrate-Based Organocatalysts

Selection of microbial biocatalysts for the reduction of cyclic and heterocyclic ketones

Applications of Carbohydrate‐Based Organocatalysts in Enantioselective Synthesis

Contact Info

Product

Resources

About