Ethylene phosphinate, hydrolysis

Optically active phosphine monoester 69 was prepared as a stable transition state analogue of the hydrolysis of 70, and used as a template (Scheme 13.17) [52], When heated in the presence of amidine 72, methyl methacrylate, ethylene glycol dimethacrylate and AIBN, polymerization took place and offered the polymer 73, in which the template 69 is attached to the binding sites by a combination of hydrogen bonds and electrostatic interactions. After washing in the presence of MeOH and aqueous NaOH, the template was removed from the cavity, thus leading to a catalytically active MIP. 

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