A fluorous, cyclative-capture strategy based on a new Pummerer cyclization process allows rapid access to tagged, heterocyclic frameworks. Convenient modification of the fluorous, heterocyclic scaffolds by using a variety of approaches including Pd-catalyzed cross-couplings is possible. Traceless, reductive cleavage of the fluorous-phase tag or oxidative cleavage and further elaboration, completes a strategy for the high-throughput, fluorous-phase synthesis of a diverse range of N-heterocycles.

An efficient, oxidative cleavage of a sulfur linker has been developed for the fluorous phase synthesis of N-heterocycles. The new cleavage strategy facilitates the synthesis of products containing diverse structural features.

SmI2 has been used to cleave a sulfur linker and trigger cyclizations in strategies for the traceless fluorous synthesis of N-heterocycles. The studies give further insights into the reactivity of samarium enolates.

A new one-pot oxidative cleavage of the sulfur linker in substrates (I) and (IV) for the fluorous phase synthesis of N-heterocycles is presented. The resulting 1,2-dicarbonyl compounds can be used as versatile substrates for further transformation. -(MCCORMICK, R. A.; JAMES, K. M.; WILLETTS, N.; PROCTER*, D. J.; QSAR Comb. Sci. 25 (2006) 8-9, 709-712; Sch. Chem., Univ. Manchester, Manchester M13 9PL, UK; Eng.) -S. Adam 02-110