Parallel kinetic resolution of an oxazolidinone using a quasi‐enantiomeric combination of [D,¹³C]‐isotopomers of pentafluorophenyl 2‐phenyl propionate

Abstract

Parallel kinetic resolution of Evans' phenylglycine derived oxazolidinone using an equimolar combination of quasi-enantiomeric active esters (derived from [D,13C]-labeled 2-phenylpropionic acid) was achieved. The levels of stereocontrol were high, leading to products with predictable configurations.

Mutual kinetic separation of isotopomers of pentafluorophenyl 2‐phenyl propionate using quasi‐enantiomeric oxazolidinones

“…The use of chiral isotopomeric probes, like 6, is important as they enable their kinetic separation to be efficiently monitored by spectroscopic methods because of their distinct physical properties. 26 We now report this particular study into the mutual kinetic recognition of an equimolar mixture of quasi-enantiomeric isotopomeric pentafluorophenyl 2-phenyl propionates 6 using a combination of quasi-enantiomeric oxazolidinones (R)-4 and (S)-5.…”

“…[12][13][14][15] Recently, a significant amount of attention has been focused on the use of traditional chiral auxiliaries [20][21][22][23][24] as potential quasienantiomeric resolving agents because of their availability in both enantiomeric forms. We have recently become interested in the complementary resolution of profen esters, 16,19,25,26 (see also Chavda et al, submitted to Chirality) such as pentafluorophenyl 2-phenylpropionate (rac)-…”

Synthesis of enantiomerically pure isotopomers of 2‐phenylpropionic acids

“…The parallel kinetic resolution of oxazolidinones, using quasi-enantiomeric isotopomers based on 1, has previously been reported elsewhere. 25,26 LITERATURE CITED…”

“…For this and a related study, 25,26 we were required to synthesize a range of enantiomerically pure [D, ]-1 which we could use as synthetic standards. We decided to use Evans' norephedrine-derived oxazolidinone (R,S)-2 as our resolving agent because of its ease of synthesis from norephedrine.…”