Highly regioselective and stereospecific functionalization of 1, 2-propanediol with trimethyl (X) silanes employing the 1, 3, 2. lambda. 5-dioxaphospholane …

I Mathieu-Pelta, SA Evans Jr

Index: Mathieu-Pelta, Isabel; Evans, Slayton A. Journal of Organic Chemistry, 1992 , vol. 57, # 12 p. 3409 - 3413

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Citation Number: 33

Abstract

The regioselective ring opening of (S)-4-methyl-2, 2, 2-triphenyl-1, 3, 2X6-dioxaphosphole (2)[prepared from the bis (transoxyph0sphoranylation) of (S)-l, 2-propanediol (l) with diethosytriphenylphoephorane (DTPP)] was initiated with several trimethylsiyl reagents (Me3SiX: X= PhS, I, Br, C1, CN, and N3) to afford the regioisomeric (sily1oxy) phosphonium salte. A stereospecific extrusion of triphenylphosphine oxide from these oxyphosphonium ...