Scalable Synthesis of Enantiomerically Pure syn-2,3-Dihydroxybutyrate by Sharpless Asymmetric Dihydroxylation of p-Phenylbenzyl Crotonate
Posted on 2011-10-21 - 00:00
An efficient four-step synthetic route to the useful chiral building block (2R,3S)-dihydroxybutyric acid acetonide in >95% ee is detailed. The sequence is readily scaled, requires no chromatography, and allows for efficient recycling of p-phenylbenzyl alcohol, an expedient for enantio- and diastereoenrichment by recrystallization.
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Smaltz, Daniel J.; Myers, Andrew G. (2016). Scalable Synthesis of Enantiomerically Pure syn-2,3-Dihydroxybutyrate by Sharpless Asymmetric Dihydroxylation of p-Phenylbenzyl Crotonate. ACS Publications. Collection. https://doi.org/10.1021/jo2016746
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