title: Efficient, stereoselective synthesis of trans-2,5-disubstituted morpholines.
abstract: [reaction: see text] Enantio- and diastereoselective syntheses of trans-2,5-disubstituted morpholine derivatives are described. The routes are initiated by the reaction of enantiopure epoxides (2) with amino alcohols (3) and address the problem of regioselective hydroxyl activation-ring closure of the resulting amino diol adducts for (amino alcohol-derived) alkyl substituents of different steric demands.
authors.affiliation: Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, USA.
authors.forename: Brian A
authors.initials: BA
authors.lastname: Lanman
authors.forename: Andrew G
authors.initials: AG
authors.lastname: Myers
mesh_terms: D000605:Amino Alcohols / Q000737:chemistry; D004852:Epoxy Compounds / Q000737:chemistry; D015394:Molecular Structure; D009025:Morpholines / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000605:Amino Alcohols; D004852:Epoxy Compounds; D009025:Morpholines