In organophosphorus chemistry, the need for flexible routes to scalemic P-stereogenic compounds has been well established.[1,2] Recently in our laboratory, it was established that chlorophosphonium salts (CPS) react rapidly with chiral non-racemic alcohols, giving unequal amounts of transient diastereomeric alkoxyphosphonium salts (DAPS),[3] which then undergo controlled collapse to either enantiomer of phosphine oxide[4] or reduction/boronation could be achieved with complete stereocontrol to give scalemic phosphane borane using lithium borohydride.  We now report that the transient DAPS can be isolated through stabilization by change of the counter ion. This intermediate could be synthesized via two routes and recrystallized into pure diastereomers, which were in turn converted to the scalemic phosphine oxides or phosphine boranes.      References: [1]      O. Berger, J.-L. Montchamp, Angew. Chem. 2013 , 125, 11587 �11590.[2]      J. Am. Chem. Soc. 2013 , 135, 2474 � 2477.[3]      K. V. Rajendran, D. G. Gilheany, Chem. Commun. 2012 , 48, 10040-10042.[4]       K. Nikitin, K. V. Rajendran, H. M�ller-Bunz, and Declan G. GilheanyAngew. Chem.   Int. Ed. 2014 , 53, 1 � 5.

Simple unprecedented preparation, isolation, and study of stablised diasteriomeric alkoxyphosphonium triflate salts

248th National Meeting (2014)

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