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Organocatalysis

ACh cover 24/2003The term organocatalysis describes the acceleration of chemical reactions through the addition of a substoichiometric quantity of an organic compound. The interest in this field has increased spectacularly in the last few years as result of both the novelty of the concept and, more importantly, the fact that the efficiency and selectivity of many organocatalytic reactions meet the standards of established organic reactions. Organocatalytic reactions are becoming powerful tools in the construction of complex molecular skeletons.[1,2]

[1] P. I. Dalko, L. Moisan,
Angew. Chem. 2001, 113, 3840; Angew. Chem. Int. Ed. 2001, 40, 3726
Angew. Chem. 2004, 116, 5248; Angew. Chem. Int. Ed. 2004, 43, 5138.

[2] Special issue of Adv. Synth. Catal. 2004, 346, Nr. 9-10.

Recent Articles

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N-Heterocyclic-Carbene-Catalyzed Redox Lactonization of o-Hydroxycinnamaldehydes and o-Hydroxycinnamyl Alcohols to Coumarins

N‐Heterocyclic‐Carbene‐Catalyzed Redox Lactonization of o‐Hydroxycinnamaldehydes and o‐Hydroxycinnamyl Alcohols to Coumarins

As quick as it gets: An N-heterocyclic-carbene (NHC)-catalyzed lactonization of o-hydroxycinnamaldehydes and o-hydroxycinnamyl alcohols afforded coumarins with distinct chemoselectivity in 30–98 % yields after 0.5 h.

[Communication]
Jingjing Meng, Qiang Jiang, Xinyang Li, Li Wan, Zheng Fang, Kai Guo
Asian J. Org. Chem., October 12, 2017, https://doi.org/10.1002/ajoc.201700458 Read article

Organocatalytic Enantioselective Protonation for Photoreduction of Activated Ketones and Ketimines Induced by Visible Light

Organocatalytic Enantioselective Protonation for Photoreduction of Activated Ketones and Ketimines Induced by Visible Light

Enantioselective protonation: The first catalytic asymmetric photoreduction of 1,2-diketones and α-keto ketimines under visible light irradiation relies on a transition-metal-free cooperative catalysis platform that harnesses dicyanopyrazine-derived chromophore (DPZ) as the photoredox catalyst and a noncovalent chiral organocatalyst. A variety of chiral α-hydroxy ketones and α-amino ketones was obtained with high yields and enantioselectivities.

[Communication]
Lu Lin, Xiangbin Bai, Xinyi Ye, Xiaowei Zhao, Choon-Hong Tan, Zhiyong Jiang
Angew. Chem. Int. Ed., October 04, 2017, https://doi.org/10.1002/anie.201707899 Read article

Organocatalytic Intramolecular [4+2] Cycloaddition between In Situ Generated Vinylidene ortho-Quinone Methides and Benzofurans

Organocatalytic Intramolecular [4+2] Cycloaddition between In Situ Generated Vinylidene ortho‐Quinone Methides and Benzofurans

Triple play: The enantioselective construction of oxygen-containing [5-6-5] tricyclic heterocycles by a thiourea-catalyzed asymmetric [4+2] cycloaddition of vinylidene ortho-quinone methides (VQMs) and benzofurans is reported. A series of oxygen-containing [5-6-5] tricyclic heterocycles having various functional groups were synthesized with excellent enantio- and diastereoselectivities.

[Communication]
Xiaoyan Wu, Lu Xue, Dongmei Li, Shiqi Jia, Jun Ao, Jun Deng, Hailong Yan
Angew. Chem. Int. Ed., September 27, 2017, https://doi.org/10.1002/anie.201707523 Read article

Organocatalytic Synthesis of Lactones by the Oxidation of Alkenoic Acids

Organocatalytic Synthesis of Lactones by the Oxidation of Alkenoic Acids

Metal-free: A green organocatalytic method for the activation of hydrogen peroxide and the oxidation of alkenoic acids to lactones is described.

[Full Paper]
Ierasia Triandafillidi, Marianna Raftopoulou, Anatoli Savvidou, Christoforos G. Kokotos
ChemCatChem, September 22, 2017, https://doi.org/10.1002/cctc.201700837 Read article

Recent Advances in Organocatalytic Glycosylations

Recent Advances in Organocatalytic Glycosylations

Despite progress in the synthesis of oligosaccharides, the efficient and stereoselective formation of glycosidic bonds by mild, nontoxic, and low-cost methods remains a challenge. This microreview presents recent advances in the application of organocatalysis to carbohydrate chemistry and in particular to the stereoselective synthesis of oligosaccharides.

[Microreview]
Ryan Williams, M. Carmen Galan
Eur. J. Org. Chem., September 08, 2017, https://doi.org/10.1002/ejoc.201700785 Read article

Selective Photooxidation Reactions using Water-Soluble Anthraquinone Photocatalysts

Selective Photooxidation Reactions using Water‐Soluble Anthraquinone Photocatalysts

A bit of SAS: Water-soluble sodium anthraquinone sulfonate is used as an organo-photocatalyst for the aerobic oxidation of alkanes and alcohols. Preliminary experiments suggest that this reaction can be extended to amines and other functionalities.

[Communication]
Wuyuan Zhang, Jenő Gacs, Isabel W. C. E. Arends, Frank Hollmann
ChemCatChem, September 07, 2017, https://doi.org/10.1002/cctc.201700779 Read article

Quinuclidine and DABCO Enhance the Radiofluorination of 5-Substituted 2-Halopyridines

Quinuclidine and DABCO Enhance the Radiofluorination of 5‐Substituted 2‐Halopyridines

Quinuclidine and DABCO are the best organic bases identified, to promote the nucleophilic substitution by [18F]fluoride ion in 5-substituted 2-halopyridines (halo = Cl or Br), and to increase the radiochemical yields to practically useful levels (> 15 %). A quaternary ammonium salt was proposed as the reaction intermediate.

[Full Paper]
Gregory R. Naumiec, Lisheng Cai, Shuiyu Lu, Victor W. Pike
Eur. J. Org. Chem., September 04, 2017, https://doi.org/10.1002/ejoc.201700970 Read article

Journey Heading Towards Enantioselective Synthesis Assisted by Organocatalysis

Journey Heading Towards Enantioselective Synthesis Assisted by Organocatalysis

[Personal Account]
Jasneet Kaur, Pankaj Chauhan, Sarbjit Singh, Swapandeep Singh Chimni
Chem. Rec., August 29, 2017, https://doi.org/10.1002/tcr.201700020 Read article

From the Studies of Hydration and Hydrolysis Reactions to the Discovery of a New Organocatalyst and Its Further Applications in Acetalization and Glycosylation

From the Studies of Hydration and Hydrolysis Reactions to the Discovery of a New Organocatalyst and Its Further Applications in Acetalization and Glycosylation

Aha! The preorganocatalyst CH3SCH2Cl/KI was discovered during an investigation into the hydration and hydrolysis reactions of glycals, enol ethers, esters, oximes, O-methyl oximes, and hydrazones in the presence of cyanuric chloride activated dimethyl sulfoxide (DMSO) as the catalyst. The precatalyst was used in acetalization reactions under wet conditions and a glycosylation reaction that is more diastereoselective than a Ferrier rearrangement.

[Full Paper]
Wenjiao Yuan, Yali Liu, Chunbao Li
Asian J. Org. Chem., July 20, 2017, https://doi.org/10.1002/ajoc.201700272 Read article

Whither Organic Synthesis?

Whither Organic Synthesis?

[Review]
Douglass F. Taber
Isr. J. Chem., April 15, 2015, https://doi.org/10.1002/ijch.201500006 Read article

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