title: Scalable synthesis of enantiomerically pure syn-2,3-dihydroxybutyrate by Sharpless asymmetric dihydroxylation of p-phenylbenzyl crotonate.
abstract: 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.
authors: Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, United States.
authors: Daniel J
authors: DJ
authors: Smaltz
authors: Andrew G
authors: AG
authors: Myers
mesh_terms: D000438:Alcohols / Q000737:chemistry; D002625:Chemistry, Organic / Q000379:methods*; D003437:Crotonates / Q000737:chemistry*; D003460:Crystallization; D006885:Hydroxybutyrates / Q000138:chemical synthesis*; D006900:Hydroxylation; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010636:Phenols / Q000737:chemistry; D059027:Recycling; D013237:Stereoisomerism
chemical_list: D000438:Alcohols; D003437:Crotonates; D006885:Hydroxybutyrates; D010636:Phenols