Phosphonamidothioic acids as thiophosphonylating agents: stereochemistry of reactions of N-tert-butyl-P-phenylphosphonamidothioic acid with alcohols

Abstract

Enantiopure PhP(S)(OH)NHBu^t reacts with alcohols in CH₂Cl₂ to give PhP(S)(OH)OR (R = Me, Prⁱ, Bu^t); reaction is completely non-stereospecific with Bu^tOH and largely so with PrⁱOH and very low concentrations of MeOH, pointing to the involvement of a thiometaphosphonate (PhPOS) intermediate.

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