Efficient, stereoselective synthesis of trans-2,5-disubstituted morpholines.
[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.
Lanman
Brian A
BA
Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, USA.
Myers
Andrew G
AG
D000605:Amino Alcohols / Q000737:chemistry; D004852:Epoxy Compounds / Q000737:chemistry; D015394:Molecular Structure; D009025:Morpholines / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism
D000605:Amino Alcohols; D004852:Epoxy Compounds; D009025:Morpholines