Bredereck-type condensation

The first report of the use of cellulose beads as support for microwave-assisted SPOS was published in 2003 and described the generation of a library of pyrazoles and isoxazoles [49]. The synthesis was performed using commercially available amino cellulose (Perloza VT-100) containing aminoaryl ethyl sulfone groups in flexible chains (Scheme 16.27). Initially, the solid support was treated with excess formyl imidazole and the corresponding yS-keto compounds to generate cellulose-bound enaminones in a one-pot Bredereck-type condensation. The reaction was catalyzed by (+)-camphor-10-sulfonic acid (CSA) and performed under microwave-irradiation conditions in an open vessel to enable the methanol formed to be removed from the reaction equilibrium [49]. 

Addition of sulfinate ions to the carbonyl group of aldehydes to form c-hydroxy sulfones (Bredereck et al., 1954, Bredereck and Bader, 1954) is also known, as is the participation of sulfinic acids as the acid component in Mannich-type condensation reactions with aldehydes (129) (Rawson and Engberts, 1970 Engberts and Strating, 1964, 1965). 

---