Regiodivergent RRM in Selective Reactions of Difunctional Substrates

Divergent RRM Using Two Chirai Reagents Paraiiei Kinetic Resolution (PKR) 

1) Preston lists the following points among the criteria for simultaneous resolution (i) (reagents) X and Y must display high degrees of chirality discrimination of opposite sense in their reactions with the substrate enantiomers (R)- and (S)-. (ii) The two 

2) Reference [61] treats consecutive as well as parallel enzymatic KR. 

To prevent interference by ChiroCLEC, the acyl carrier intended for phosphine activation (the mixed mesitoate anhydride 212) was placed on an insoluble solid support where it can be accessed by the soluble phosphine, but not by the insoluble ChiroCLEC. Under three phase conditions, interference was prevented because the phosphine does not activate vinyl pivalate, the acyl donor intended for activation by ChiroCLEC in the form of an activated ester 214 nor does the activated acylphosphonium species 213 come into contact with the ChiroCLEC. Potential destruction of the lipase catalyst is thereby avoided, and the enantio-complementary activated intermediates convert the racemic alcohol R,S)-7 into the solid phase-bound ester 215 and the soluble pivalate 216 with excellent enantioselectivity. This is a proof-of-concept experiment that demonstrates the most difficult application, the case where two similar catalytic reactions are conducted in parallel. Furthermore, the experiment demonstrates PKR with the incorporation of achiral subunits to achieve enantiodivergence, and achieves product separation by simple filtration. 

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