Resins TentaGel

Moberg et al. [146] modified further the bis(pyridylamide) ligand described by Trost for the preparation of a polymer-supported pyridylamide (113 in Scheme 60) for the microwave-accelerated molybdenum-catalyzed al-lylic alkylation. TentaGel resin was tested in the presence of high concentrations of reactants and gave, after a 30 min reaction, total conversion in the... 

Tripeptides with N-terminal anthranilic acid part were used as starting materials in the solid-phase synthesis carried out on TentaGel resin to prepare 1,4,11,1 l -tetrahydro-2//-pyrazino[2,l-3]quinazoline-3,6-diones with various N-l and N-3 substituents <2003EPP1471066>. Tandem cyclization from [6+0] atom fragments took place in the solid-phase synthesis of 143 from 142. Intermediate 141 was built on bromoacetal resin (Scheme 17) <1998JOC3162>. 

Table 9.1 shows the method s versatility across several solid-support types. Care must be taken to dry the tentagel resins by lyophilization for 24 h before subjecting them to the reaction conditions. In the examples shown, quantitative conversions were obtained as determined by elemental analysis and 13C NMR. The mild reaction conditions are most evident by the quantitative conversion of SASRIN resin to its corresponding chloromethyl... 

FIGURE 5.10 Synthesis of a polyethyleneglycol-polystyrene graft polymer by etherification of Merrifield resin using potassium tetra(oxyethylene) oxide, followed by extension of the chain by reaction of the potassium salt, which is present as the crown ether.21 In several TentaGel resins, the connecting bond is an ethyl ether that is more acid-stable than the benzyl ether. 

This dual linker approach allowed selective cleavage of the peptide from the dendrimer using 1% TFA/CH2CI2 without cleaving the dendrimer from the resin. Proceeding from the TentaGel resin the final product was obtained in 44% yield... 

The o-fluoro-nitroarene was attached to TentaGel resin as a phenolic ether 73 via a modified Wang-type linker. Following aminolysis of 73, reduction of the intermediate nitroaniline to di-aniline 74 proceeded poorly... 

Fmoc-AzSar-Asp(Bu)-amide Photolinker TentaGel Resin (26, R1=Fmoc R2=Me R =H ... 

They produced an 18-member library of a-acylamino amides, in acceptable to high yields and purity, from a variety of isocyanides, aldehydes and carboxylic acids by using an amino-functionalised TentaGel resin (TentaGel S RAM). The developed procedure represents a rapid and efficient way of synthesising a-acylamino amides, simplifying the tedious purifications, which can usually accompany multi-component reactions. 

We recently reported the synthesis of a perfluoroalkylsulfonyl linker attached to TentaGel resin 13 (Fig. 6), which proves to act in a fashion similar to triflates as we had hoped, and demonstrated its application for the traceless cleavage of phenols using palladium-catalyzed reduction and Suzuki cross-coupling reactions.3,4... 

All starting materials were obtained from Aldrich (Milwaukee, WI). TentaGel resin was obtained from Rapp Polymere (Tubingen, Germany). Procedures for the synthesis of the PFS linker and its attachment to resin to form 13 have been previous described.3... 

---