Synthesis of enantiopure 3-substituted morpholines.
Enantiopure 3-substituted morpholines were assembled through ring-opening of a N-2-benzothiazolesulfonyl (Bts) activated aziridine with organocuprates followed by a ring annulation reaction with a vinylsulfonium salt under microwave conditions. Deprotection of the N-Bts group proceeds under very mild conditions with 2-mercaptoacetic acid and LiOH at rt.
Bornholdt
Jan
J
Department of Medicinal Chemistry, University of Copenhagen, Universitetsparken 2, Copenhagen DK-2100, Denmark.
Felding
Jakob
J
Kristensen
Jesper Langgaard
JL
D052160:Benzothiazoles / Q000737:chemistry; D009025:Morpholines / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
D052160:Benzothiazoles; D009025:Morpholines; C037574:morpholine; C005465:benzothiazole