154550-36-4Relevant academic research and scientific papers
Easy preparation of enantiopure C2 symmetrical hydroxy and amino sulfides derived from ephedrine and their application in a Pd catalyzed coupling reaction
Koning, Bartjan,Hulst, Ron,Kellogg, Richard M.
, p. 49 - 55 (2007/10/03)
Ephedrine can be readily converted by means of intramolecular SN2 substitution by the hydroxyl or amino substituent into, respectively, the corresponding epoxide or aziridine with high stereocontrol. Subsequent stereoselective ring opening at the benzylic centre using tetrabutyl-ammonium fluoride (TBAF) and dithiols affords the C2 symmetrical hydroxy or amino sulfides in excellent yield. Application of these ligands in a palladium-catalyzed asymmetric allylic substitution reaction gave moderate to high enantiomeric excesses (up to 79%) and high yields of product.
ENANTIOMERICALLY PURE β-AMINO SULFIDES AND β-AMINO THIOLS FROM EPHEDRINE
Poelert, Martin A.,Hof, Robert P.,Peper, Nathalie C. M. W.,Kellogg, Richard M.
, p. 461 - 476 (2007/10/02)
Ephedrine and pseudoephedrine are converted by means of a Mitsunobu reaction to respectively trans- and cis-aziridines, which can be ring-opened at the benzylic center with inversion of configuration by thiols and thiol acids.The trans-aziridine from ephe
