Scalable Synthesis of Enantiomerically Pure syn-2,3-Dihydroxybutyrate by Sharpless Asymmetric Dihydroxylation of p-Phenylbenzyl Crotonate

Scalable Synthesis of Enantiomerically Pure syn-2,3-Dihydroxybutyrate by Sharpless Asymmetric Dihydroxylation of p-Phenylbenzyl Crotonate

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 diaste...

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Veröffentlicht in:Journal of organic chemistry 2011-10, Vol.76 (20), p.8554-8559
Hauptverfasser: Smaltz, Daniel J, Myers, Andrew G
Format: Artikel
Sprache:eng
Schlagworte:
Alcohols - chemistry
Aliphatic compounds
Chemistry
Chemistry, Organic - methods
Crotonates - chemistry
Crystallization
Exact sciences and technology
Hydroxybutyrates - chemical synthesis
Hydroxylation
Magnetic Resonance Spectroscopy
Molecular Structure
Noncondensed benzenic compounds
Organic chemistry
Phenols - chemistry
Preparations and properties
Recycling
Stereoisomerism
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Zusammenfassung: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo2016746