6533b831fe1ef96bd1298421
RESEARCH PRODUCT
Asymmetric synthesis of (−)-pseudoephedrine from (2S,3S)-3-phenyloxiran-2-ylmethanol. Stereospecific interchange of amino and alcohol functions
Ana Belén Garcı́a-segoviaMaria Luisa TestaChakib HajjiJosé Sepúlveda-arquesElena Zaballos-garcíasubject
Inorganic Chemistrychemistry.chemical_compoundStereospecificityChemistryStereochemistryOrganic ChemistryEnantioselective synthesismedicineAlcoholPhysical and Theoretical ChemistryPseudoephedrineCatalysismedicine.drugdescription
Abstract A ring-opening reaction of N -methylaziridines with Boc 2 O/NaI has been applied to the asymmetric synthesis of pseudoephedrine. 3-Methylamino-3-phenyl-1,2-propanediol 1 , derived from (2 S ,3 S )-3-phenyloxiran-2-ylmethanol, was converted into the oxazolidin-2-one 4 , a precursor of pseudoephedrine. The reaction occurs with a stereospecific interchange of amino and alcohol functions.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2001-06-01 | Tetrahedron: Asymmetry |