Highly Enantioselective Synthesis of N‐Protected β‐Amino Malonates Catalyzed by Magnetically Separable Heterogeneous Rosin‐Derived Amino Thiourea Catalysts: A Stereocontrolled Approach to β‐Amino Acids

Zhu, Hao; Jiang, Xianxing; Li, Xinghua; Hou, Chen; Jiang, Yu; Hou, Ke; Wang, Rui; Liu, Yanfeng

doi:10.1002/cctc.201300089

Cited by 19 publications

(12 citation statements)

References 81 publications

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“…Moreover, rosin-derived thioureas can be used as enantioselective catalysts for many reactions [12]. In recent years these were: Michael addition [223,224], tandem Michael/cyclization sequence [225], asymmetric Michael/hemiketalization [226], asymmetric aza-Henry reaction [227], asymmetric tandem reaction [228], Mannich reaction [229,230], Friedel–Crafts alkylation [231], enantio- and diastereoselective asymmetric addition [232], as well as synthesis of chiral amines [233] or N -protected β-amino malonates [234]. In recent studies rosin-derived thioureas are dominant majority of all investigated rosin-derived catalysts.…”

Section: Rosin-based Chemicalsmentioning

confidence: 99%

Advances in Rosin-Based Chemicals: The Latest Recipes, Applications and Future Trends

et al. 2019

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A comprehensive review of the publications about rosin-based chemicals has been compiled. Rosin, or colophony, is a natural, abundant, cheap and non-toxic raw material which can be easily modified to obtain numerous useful products, which makes it an excellent subject of innovative research, attracting growing interest in recent years. The last extensive review in this research area was published in 2008, so the current article contains the most promising, repeatable achievements in synthesis of rosin-derived chemicals, published in scientific literature from 2008 to 2018. The first part of the review includes low/medium molecule weight compounds: Especially intermediates, resins, monomers, curing agents, surfactants, medications and biocides. The second part is about macromolecules: mainly elastomers, polymers for biomedical applications, coatings, adhesives, surfactants, sorbents, organosilicons and polysaccharides. In conclusion, a critical evaluation of the publications in terms of data completeness has been carried out with an indication of the most promising directions of rosin-based chemicals development.

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Section: Rosin-based Chemicalsmentioning

confidence: 99%

Advances in Rosin-Based Chemicals: The Latest Recipes, Applications and Future Trends

et al. 2019

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“…View Article Online reaction was described, starting from racemic N-Boc (N-tertbutoxycarbonyl) protected α-amino sulfones 141 and 92 using optically pure 1,2-cyclohexanediamine-thiourea derivative bonded on the surface of Fe 3 O 4 MNPs (CT29*). 187 In reactions of aromatic α-amino sulfones, high yields and enantioselectivities were obtained (Scheme 41). The easily separated chiral magnetic catalyst was recycled 14 times without a decrease in performance.…”

Section: 181mentioning

confidence: 99%

Asymmetric one-pot reactions using heterogeneous chemical catalysis: recent steps towards sustainable processes

Szőllősi

2018

Catal. Sci. Technol.

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The preparation of optically pure fine chemicals is among the most important and challenging tasks met by organic chemists. Recently, significant efforts have been focused on the development of green and sustainable procedures for the synthesis of these high value-added compounds. Asymmetric heterogeneous catalysis has provided efficient solutions to these challenges. The application of heterogeneous chiral catalysts in one-pot processes combines the advantages of use of these materials with time, material, and energy savings associated with cascade or sequential procedures. This review surveys these asymmetric onepot reactions reported until July 2017, in which a heterogeneous chemical catalyst has been applied either as a single multifunctional catalyst or in combination with a second catalytically active material. These processes include one-pot procedures catalysed by carefully designed solids obtained by the immobilization of chiral metal complexes, by anchoring chiral organocatalysts, or by modifying catalytic surfaces with optically pure compounds, which may also incorporate uncatalyzed and homogeneously catalysed steps. Methods applying achiral heterogeneous catalysts in combination with soluble chiral chemical catalysts or biocatalysts are also presented. Sophisticated, finely tuned materials have been applied in most of these reactions, which have been discussed along with the main requirements necessary to perform these transformations in a one-pot manner.

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“…A rosin‐derived tertiary amino thiourea catalyst has been supported onto magnetic nanoparticles in order to generate the heterogeneous catalyst ( XXI ). This compound has been employed in the enantioselective synthesis of chiral β‐amino acids (Scheme ) by means of in situ generation of carbamate‐protected imine from aromatic amido sulfones ( 37 ), which react with dibenzyl malonate ( 9 d ) in a Mannich reaction . For this heterogeneous reaction, good to excellent yields (80‐92 %) and high enantioselectivities (>90 % ee ) were obtained depending on the amido sulfone structure.…”

Section: Magnetic Nanoparticles As Carriers Of Hydrogen‐bond Catalystsmentioning

confidence: 99%

Recent Developments on Supported Hydrogen‐bond Organocatalysts

Franconetti

Gonzalo

2018

ChemCatChem

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Hydrogen‐bond organocatalysts are a family of Brønsted acid organic compounds able to activate electrophilic substrates toward nucleophilic addition through hydrogen bonding interactions. Since the first report using these catalysts, they have been widely exploited in several valuable processes, in general with high activities and selectivities. The immobilization of hydrogen‐bond catalysts affords heterogeneous systems which enable different features for a green chemistry approach, such as chemical and mechanical stability, easy work‐up and/or reusability. Several kinds of supports have been employed for immobilization while maintaining the advantages of the homogeneous catalysts. In the present review, we have mainly focused our attention in the immobilization of ureas, thioureas and squaramides organocatalysts onto various supports, including polymeric materials, mesoporous silicas, nanoparticles and ionic liquids, and also some copolymerization processes have been described. In addition, the role of these supported organocatalysts published since 2010 on different stereoselective transformations has been evaluated.

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Highly Enantioselective Synthesis of N‐Protected β‐Amino Malonates Catalyzed by Magnetically Separable Heterogeneous Rosin‐Derived Amino Thiourea Catalysts: A Stereocontrolled Approach to β‐Amino Acids

Abstract: A rosin by any other name: Magnetic‐nanoparticle‐supported bifunctional rosin‐derived tertiary amino thiourea catalysts are developed for the stereocontrolled synthesis of chiral β‐amino acids. Boc=tert‐butoxycarbonyl, Bn=benzyl.

Cited by 19 publications

References 81 publications

Advances in Rosin-Based Chemicals: The Latest Recipes, Applications and Future Trends

Advances in Rosin-Based Chemicals: The Latest Recipes, Applications and Future Trends

Asymmetric one-pot reactions using heterogeneous chemical catalysis: recent steps towards sustainable processes

Recent Developments on Supported Hydrogen‐bond Organocatalysts

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