66295-45-2Relevant academic research and scientific papers
SYNTHESIS, REACTIONS, AND STEREOCHEMICAL CORRELATIONS OF AN OPTICALLY ACTIVE TERVALENT PHOSPHORUS THIO ESTER
Szafraniec, Leonard J.,Szafraniec, Linda L.,Aaron, Herbert S.
, p. 177 - 184 (2007/10/02)
The tetracovalent (R)-(-)-isopropyl methylphosphionate (2) reacts with methyl trifluoromethanesulfonate to form a phosphonium salt (3), which yields the tervalent (R)-(-)-O-isopropyl S-methyl methylphosphonothioite (4) on treatment with triethylamine.However, the reaction is much less sterespecific (ca. 35percent) than that of the corresponding P=O analog, 1 (ca. 100percent).The (-)-4 product was characterized and its configuration confirmed by conversion into its corresponding P=O and P=S derivatives, (S)-(-)-5 and (R)-(-)-8, respectively, which have been related to the known (S)-(-) and (R)-(+)- O-isopropyl methylphosphnothioic acids (6).The triflate product has also been prepared by a relatively simple asymmetric induction reaction that had been reported for a similar compound, and the stereospecificities of the two procedures are compared.
