Abstract
We report the stereochemistry of reactions of various nucleophiles with optically active silyl esters of phosphorus of general formula: tBuPhP(X)OSiMePhNp (X = −(1), Oxygen (2), Sulfur (3), Selenium (4). The list of nucleophiles includes O,S,N,C nucleophiles as well as halides. The nucleophilic attack is essentially directed towards silicon. The phosphinous and phosphonic acid esters react with predominant retention of configuration at silicon atom, whereas the thiono and seleno phosphinic analogues give inversion at silicon centre. The stereochemical crossover is explained in terms of possible interaction of the electrophilic part of the nucleophile with the oxyphosphoryl group or tricoordinate phosphorus.
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