Abstract
A highly enantioselective (up to 97% ee) one-step synthesis of paclitaxel side chain precursor, (2 R,3 S)-isopropyl 3-benzamido-2-hydroxy-3-phenylpropionate, has been achieved by osmium-catalyzed asymmetric aminohydroxylation of isopropyl trans-cinnamate with N-bromobenzamide as an oxidant/nitrogen source in the presence of (DHQ) 2PHAL as a chiral ligand. Simple recrystallization of crude product (containing regioisomer and diol) from ethyl acetate gave the enantiomerically pure product.
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