From Silylphosphanes and Oxazolones to New Phosphorus Amido-Acids

Silylphosphanes 3 and 4 gave 1,4-additions with the O=C-C=C moiety of oxazolones 1a-e and 2a-f to afford the adducts 5–8. Oxidation or sulfuration of 5–8 followed by hydrolysis led to oxyphosphorus (or thiophosphorus) amido-acids 9–11 and 15, 19, 20 respectively. A great difference was observed in the behaviour of thiophosphane oxides 16 (R = Me) and 17(R = Ph) toward hydrolysis: 16 led directly to the amido-acid 19 by opening of the lactonic ring whereas, from 17, the heterocyclic intermediate 18 could be isolated.