A convenient route to the phosphorus and sulfur stereoisomers of ethyl menthyl (methylsulfinyl)methylphosphonate

Add time:07/22/2019    Source:sciencedirect.com

The four phosphorus and sulfur stereoisomers of ethyl menthyl (methylsulfinyl)methylphosphonate were obtained by preparing the corresponding sulfides from commercially available diethyl (methylthio)methylphosphonate and subjecting them to a highly diastereoselective hydroperoxide oxidation in the presence of catalytic amounts of a titanium (R)- or (S)-BINOL complex. The configuration at the sulfur stereogenic centre was assigned by a chemical correlation based upon a displacement reaction with Grignard reagents, whereas the configuration at the phosphorus stereogenic centre was assigned by taking advantage of a reaction sequence based upon the use of menthyl (RP)-methylphosphonothioic acid as a starting material.

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