Using L-menthol as a consistent source of chirality, classical methods for generating chirality at phosphorus are compared to dynamic kinetic resolution methods reported recently from our laboratory.Classic Resolution:Direct addition of the auxiliary to an achiral PIII or PV centre such that the auxiliary remains attached to the stereochemically enriched PV product.1                                                      Dynamic Kinetic Resolution:Racemic P-stereogenic starting material (PIII or PV) is converted to rapidly racemising chlorophosphonium salts (CPS). Reaction with the auxiliary gives diastereomeric alkoxy phosphonium salts (DAPS), which then undergo Arbuzov collapse to enantioenriched phosphine oxide.2                                                      Use of NR2/OR/OAr as the R' moieties allow synthesis towards compounds in the nucleotide prodrug class. A complication arising when R' is NR2, and using (COCl)2,is that HCl produced cleaves the amine moeity.[1] Korpiun, O.; Lewis, R. A.; Chickos, J.; Mislow, K., J. Am. Chem. Soc., 1968 , 90, 4847-4853.[2] Nikitin, K.; Rajendran, K. V.; M�ller-Bunz, H.; Gilheany, D. G., Angew. Chem. Int. Ed., 2014 , 53, 1906-1909.

Comparison of techniques for <i>P</i>-stereogenic phosphorus compounds

248th National Meeting (2014)

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Comparison of techniques for P-stereogenic phosphorus compounds