Synthesis fluorous

Fluorous synthesis has certain analogies to solid-phase synthesis the fluorous label and the fluorous phase fulfil functions similar to those of the linker and the solid phase in that both provide a means of removing the attached compound from the reaction mixture (one because of its high affinity to the fluorous phase, the other via a covalent link to the solid support).The similarity, however, also extends to the necessity of additional synthesis steps involved in the attachment to and cleavage from the linker. Otherwise, the fluo- 

Fluorous synthesis protocols for combinatorial chemistry have been developed for various reactions  

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A. Studer, S. Hadida, R. Ferritto, S.Y. Kim, P. Jeyer, P. Wipf, D.P. Curran, Fluorous synthesis — A fluorous-phase strategy for improving separation efficiency in organic synthesis. Science 275 823-826 1997. 

Fluorous Synthesis of Biaryl-Subshtuted Proline Analogs. 112... 

Fluorous Synthesis of Biaryl-Substituted Proline Analogs... 

Fig. 30 Microwave-promoted fluorous synthesis of biaryl-subshtuted proline analogs. Reagents and condihons a EtaN, DMF, MW 150 °C, 15 min, 40-75%, closed vials b R""PhB(OH)2, Pd(dppf)Cl2, K3PO4, toluene Acetone H2O, MW 120 °C, 12 min, sealed vial system, 19-79%. R=Me, Et R = Me, 1 - Pr R" = H, 3-MeO R" =Me, Et R""= 4-MeO, 3-Cl, 4-Ac,3,4-diCl,3,4-methylenedioxy...

Fluorous Synthesis of Dihydropteridinones by Microwave-Assisted Cyclative Cleavage... 

By replacing insoluble cross-linked resins with soluble polymer supports, the well-estabhshed reaction conditions of classical organic chemistry can be more readily apphed, while still fadhtating product purification. However, soluble supports suffer from the hmitation of low loading capacity. The recently introduced fluorous synthesis methodology overcomes many of the drawbacks of both the insoluble beads and the soluble polymers, but the high cost of perfluoroalkane solvents, hmitation in solvent selection, and the need for specialized reagents may hmit its apphcations. 

Dichloro-2( lff)-pyrazinones 273 Dihydropteridinones, fluorous synthesis, cyclative cleavage 113... 

Proline analogs, biaryl-substituted, fluorous synthesis 112 PS-anthracene, dienophiles 151 PS-carbodiimide 136 Pimine C-2, nucleophilic displacement 119... 

Maul JJ, Ostrowski PJ, Ublacker GA, Linclau B, Curran DP (1999) Benzotrifluoride and Deri-vates Useful Solvents for Organic Synthesis and Fluorous Synthesis. 206 79-105 McDonnell KA, see Imperiali B (1999) 202 1-38 McKelvey CA, see Hentze H-P (2003) 226 197-223... 

Zhang W (2006) Microwave-Enhanced High-Speed Fluorous Synthesis. 266 145-166 Zhang X-E, Deng J-Y (2005) Detection of Mutations in Rifampin-Resistant Mycobacterium Tuberculosis by Short Oligonucleotide Ligation Assay on DNA Chips (SOLAC). 261 169-190... 

Curran DP, Luo ZY (1999) Fluorous Synthesis with Fewer Fluorines (Light Flu-orous Synthesis) Separation of Tagged from Untagged Products by Solid-Phase Extraction with Fluorous Reverse-Phase Silica Gel. J Am Chem Soc 121 9069-9072... 

Wiles C, Watts P, Wiles C, Haswell S, Pombo-Villar E (2001) The Aldol Reaction of Silyl Enol Ethers within a Microreactor. Lab Chip 1 100-101 Zhang W (2004) Fluorous Synthesis of Heterocyclic Systems. Chem Rev 104 2531-2556... 

Keywords m Fluorous BiphasicCatalysis m Fluorous Synthesis m Combinatorial Chemistry... 

The first demonstration of fluorous synthesis was in the preparation of small (8-12 members) isoxazo-line and isoxazole libraries by the three-step procedure outlined in Figure 8.1461 All reactions were purified by three-phase liquid-liquid extraction. The starting substrates were simple allylic alcohols which were tagged with the fluorous silyl halide 5 to make substrates 6 for an ensuing dipolar cycloaddition. This was conducted by the Mukaiyama method with a large excess of nitro compound and... 

By analogy to the usual usage of solid phase synthesis , we intend "fluorous synthesis to mean techniques in which the substrate or product is fluorous. However, the term fluorous synthesis is also sometimes used more broadly to encompass essentially any fluorous technique... 

A. Studer, D. P. Curran, A Strategic Alternative to Solid Phase Synthesis Preparation of A Small Isocazoline Library by Fluorous Synthesis , Tetrahedron 1997, 53, 6681... 

A. Studer, P. Jeger, P. Wipf, D. P. Curran, Fluorous Synthesis Fluorous Protocols for the Ugi and Biginelli Multicomponent Condensations ,/. Org. Chem. 1997,62,2917. 

D. P. Curran, R. Ferritto, Y. Hua, Preparation of a Eluor-ous Benzyl Protecting Group and its Use in a Fluorous Synthesis Approach to a Disaccharide , Tetmzhedron Lett. 1998, 39, 4937. 

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