Fluorinated fluorous mixture synthesis

Manku, S. and Curran, D. P. (2005) Fluorous mixture synthesis of fused-tricyclic hydantoins. Use of a redundant tagging strategy on fluorinated substrates../. Org. Chem., 70, 4470-4473. 

Scheme 7.5 Fluorous mixture synthesis of fluorinated dendrimers.

In addition to the en route protocol described in Section 13.2.6 for the synthesis of pas-sifloricins, the use of redundant tags for the synthesis of fused-tricyclic hydantoins is another example of FMS in which the number of fluorous tags is less than that of components in the mixture. Since molecules for FMS have fluorine atoms both on the parent structure and on the tag, each component in the mixture has different total fluorine content - even the tag may be redundant. 

Choosing fluoiinated substrates, soluble in fluorinated solvents, Curran et al. have used fluorous-phase chemistry toward the synthesis of DHPMs. The reaction mixture was purified by a liquid-liquid extraction method because by-products were not soluble in fluorinated solvents. Reaction of fluorinated urea 16 with alkyl acetoacetate and an aldehyde. 

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