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The influence of DBU on configurational stability of P‐chiral organophosphates requires further study. Unpublished results from our laboratory (Z. J. Lesnikowski, L. Wozniak) indicate that diastereomers of dinucleoside 3′,5′‐methanephosphonates are not epimerized in the presence of DBU under conditions that lead to complete P‐epimerization of diastereomerically pure nucleoside 3′‐O‐(O‐4‐nitrophenylmethanephosphonate)s or nucleoside 3′‐O‐(Se‐methyl‐methanephosphonate)s. Therefore, these last results can be explained in terms of DBU‐catalyzed hydrolysis caused by traces of water; released p‐nitrophenoxide ion or methylselenenyl ion, respectively, may cause epimerization of parent compounds in the presence of DBU by a ping‐pong type mechanism.
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