title: Deuterium as a Stereochemically Invisible Blocking Group for Chiral Ligand Synthesis.
abstract: Highly diastereoselective lithiation (s-BuLi/TMEDA in Et2O, -78 °C, 2 h) of (S)-2-ferrocenyl-4-(substituted)oxazolines followed by addition of MeOH-d4gave up to 95% D incorporation. Subsequent application of alternative lithiation conditions (n-BuLi in THF, -78 °C, 2 h), followed by addition of an electrophile, resulted in a reversal of diastereoselectivity controlled primarily by the high kH/kDvalue for lithiation (isomer ratio typically between 10:1 and 20:1).
authors.affiliation: School of Chemistry, University of East Anglia , Norwich Research Park, Norwich NR4 7TU, U.K.
authors.forename: Ross A
authors.initials: RA
authors.lastname: Arthurs
authors.affiliation: School of Chemistry, University of East Anglia , Norwich Research Park, Norwich NR4 7TU, U.K.
authors.forename: Christopher J
authors.identifier: 0000-0001-7899-4082
authors.initials: CJ
authors.lastname: Richards