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Literature DB >> 20198422

Expanding cyclitol structural diversity by biocatalysis and metalocatalysis. A click chemistry approach.

Victoria de la Sovera¹, Ana Bellomo, Jesus M Pena, David Gonzalez, Hélio A Stefani.

Abstract

The palladium catalyzed cross-coupling reaction of phenyltrifluoroborate with a chemoenzymatically derived bromoazidoconduritol, combined with 1,3-dipolar cycloaddition, with a variety of alkynes is described. Fourteen new compounds were synthesized in moderate to good yields. The click chemistry reaction can be effected by using sodium ascorbate and CuSO(4) · 5H(2)O as catalyst in toluene-H(2)O at room temperature.

Entities: Chemical

Mesh：

Substances：

Year: 2010 PMID： 20198422 DOI： 10.1007/s11030-010-9237-6

Source DB: PubMed Journal: Mol Divers ISSN： 1381-1991 Impact factor: 2.943

13 in total

1. Click Chemistry: Diverse Chemical Function from a Few Good Reactions.

Authors: Hartmuth C. Kolb; M. G. Finn; K. Barry Sharpless
Journal: Angew Chem Int Ed Engl Date: 2001-06-01 Impact factor: 15.336

2. "Clickphine": a novel and highly versatile P,N ligand class via click chemistry.

Authors: Remko J Detz; Silvia Arévalo Heras; R de Gelder; Piet W N M van Leeuwen; Henk Hiemstra; Joost N H Reek; Jan H van Maarseveen
Journal: Org Lett Date: 2006-07-20 Impact factor: 6.005

3. Inhibitors of HIV-1 protease by using in situ click chemistry.

Authors: Matthew Whiting; John Muldoon; Ying-Chuan Lin; Steven M Silverman; William Lindstrom; Arthur J Olson; Hartmuth C Kolb; M G Finn; K Barry Sharpless; John H Elder; Valery V Fokin
Journal: Angew Chem Int Ed Engl Date: 2006-02-20 Impact factor: 15.336

4. Evolution of pyrrolidine-type asymmetric organocatalysts by "click" chemistry.

Authors: Sanzhong Luo; Hui Xu; Xueling Mi; Jiuyuan Li; Xiaoxi Zheng; Jin-Pei Cheng
Journal: J Org Chem Date: 2006-11-24 Impact factor: 4.354

5. Copper(I)-catalyzed synthesis of azoles. DFT study predicts unprecedented reactivity and intermediates.

Authors: Fahmi Himo; Timothy Lovell; Robert Hilgraf; Vsevolod V Rostovtsev; Louis Noodleman; K Barry Sharpless; Valery V Fokin
Journal: J Am Chem Soc Date: 2005-01-12 Impact factor: 15.419

6. Combining Biginelli multicomponent and click chemistry: generation of 6-(1,2,3-triazol-1-yl)-dihydropyrimidone libraries.

Authors: Bogdan Khanetskyy; Doris Dallinger; C Oliver Kappe
Journal: J Comb Chem Date: 2004 Nov-Dec

Expanding cyclitol structural diversity by biocatalysis and metalocatalysis. A click chemistry approach.

1. Click Chemistry: Diverse Chemical Function from a Few Good Reactions.

2. "Clickphine": a novel and highly versatile P,N ligand class via click chemistry.

3. Inhibitors of HIV-1 protease by using in situ click chemistry.

4. Evolution of pyrrolidine-type asymmetric organocatalysts by "click" chemistry.

5. Copper(I)-catalyzed synthesis of azoles. DFT study predicts unprecedented reactivity and intermediates.

6. Combining Biginelli multicomponent and click chemistry: generation of 6-(1,2,3-triazol-1-yl)-dihydropyrimidone libraries.

7. New access to 1-deoxynojirimycin derivatives via azide-alkene cycloaddition.

Review 8. The growing impact of click chemistry on drug discovery.

Review 9. The growing applications of click chemistry.

10. A concise route to triazolobenzodiazepine derivatives via a one-pot alkyne-azide cycloaddition reaction.

1. Synthesis of novel 6-triazologlycolipids via click chemistry and their preliminary cytotoxicity assessments.

Review 2. Bio-click chemistry: a bridge between biocatalysis and click chemistry.