Literature DB >> 34885873

Synthesis and Applications of Carbohydrate-Based Organocatalysts.

Elżbieta Wojaczyńska1, Franz Steppeler1, Dominika Iwan1, Marie-Christine Scherrmann2, Alberto Marra3.   

Abstract

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.

Entities:  

Keywords:  Darzens condensation; Diels–Alder reaction; Michael addition; Strecker reaction; aldol reaction; chitosan; cinchona alkaloids; phase-transfer catalysis; proline; thioureas

Mesh:

Substances:

Year:  2021        PMID: 34885873      PMCID: PMC8659088          DOI: 10.3390/molecules26237291

Source DB:  PubMed          Journal:  Molecules        ISSN: 1420-3049            Impact factor:   4.411


  84 in total

1.  Synthesis and conformational analysis of cyclic homooligomers from pyranoid ε-sugar amino acids.

Authors:  Andrés Feher-Voelger; Jorge Borges-González; Romen Carrillo; Ezequiel Q Morales; Javier González-Platas; Tomás Martín
Journal:  Chemistry       Date:  2014-02-25       Impact factor: 5.236

2.  Synthesis and biological evaluation of deoxy salacinols, the role of polar substituents in the side chain on the alpha-glucosidase inhibitory activity.

Authors:  Osamu Muraoka; Kazuya Yoshikai; Hideo Takahashi; Toshie Minematsu; Guangxin Lu; Genzoh Tanabe; Tao Wang; Hisashi Matsuda; Masayuki Yoshikawa
Journal:  Bioorg Med Chem       Date:  2005-09-29       Impact factor: 3.641

3.  An efficient, inexpensive, and shelf-stable diazotransfer reagent: imidazole-1-sulfonyl azide hydrochloride.

Authors:  Ethan D Goddard-Borger; Robert V Stick
Journal:  Org Lett       Date:  2007-08-22       Impact factor: 6.005

4.  Novel amphiphilic cyclic oligosaccharides: synthesis and self-aggregation properties.

Authors:  Cinzia Coppola; Vittorio Saggiomo; Giovanni Di Fabio; Lorenzo De Napoli; Daniela Montesarchio
Journal:  J Org Chem       Date:  2007-11-08       Impact factor: 4.354

5.  Synthesis of ribo-hexopyranoside- and altrose-based azacrown ethers and their application in an asymmetric Michael addition.

Authors:  Zsolt Rapi; Péter Bakó; György Keglevich; Áron Szöllősy; László Drahos; László Hegedűs
Journal:  Carbohydr Res       Date:  2012-11-08       Impact factor: 2.104

6.  Ketone-catalyzed asymmetric epoxidation reactions.

Authors:  Dan Yang
Journal:  Acc Chem Res       Date:  2004-08       Impact factor: 22.384

7.  Enantioselective epoxidation of conjugated cis-enynes by chiral dioxirane.

Authors:  Christopher P Burke; Yian Shi
Journal:  J Org Chem       Date:  2007-04-26       Impact factor: 4.354

8.  An efficient route to pyrimidine nucleoside analogues by [4 + 2] cycloaddition reaction.

Authors:  Morwenna S M Pearson; Aélig Robin; Nathalie Bourgougnon; Jean Claude Meslin; David Deniaud
Journal:  J Org Chem       Date:  2003-10-31       Impact factor: 4.354

9.  Enantioselective aza-Henry reaction catalyzed by a bifunctional organocatalyst.

Authors:  Tomotaka Okino; Satoru Nakamura; Tomihiro Furukawa; Yoshiji Takemoto
Journal:  Org Lett       Date:  2004-02-19       Impact factor: 6.005

10.  Enantioselective organocatalytic oxidation of functionalized sterically hindered disulfides.

Authors:  Noureddine Khiar; Siham Mallouk; Victoria Valdivia; Khalid Bougrin; Mohammed Soufiaoui; Inmaculada Fernández
Journal:  Org Lett       Date:  2007-03-07       Impact factor: 6.005

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  1 in total

Review 1.  On the Origin of Sugar Handedness: Facts, Hypotheses and Missing Links-A Review.

Authors:  R Fernando Martínez; Louis A Cuccia; Cristóbal Viedma; Pedro Cintas
Journal:  Orig Life Evol Biosph       Date:  2022-07-07       Impact factor: 1.120

  1 in total

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