title: One pot synthesis of amino acid derived chiral disubstituted morpholines and 1,4-oxazepanes via tandem aziridine/epoxide ring opening sequences.
abstract: A new one-pot synthetic strategy is described for the synthesis of enantiomerically pure cis-3,5-disubstituted morpholines and 3,6-disubstituted 1,4-oxazepanes via tandem aziridine/epoxide ring opening sequences. This new strategy describes how epoxy alcohols could act as both a nucleophile and an electrophile in a tandem fashion and undergo intermolecular regioselective ring opening of chiral aziridines for the first time.
authors.affiliation: Medicinal and Process Chemistry Division, CSIR, Central Drug Research Institute, Lucknow, 226001, UP, India.
authors.forename: Krishnananda
authors.initials: K
authors.lastname: Samanta
authors.forename: Gautam
authors.initials: G
authors.lastname: Panda
mesh_terms: D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D001388:Aziridines / Q000737:chemistry*; D004852:Epoxy Compounds / Q000737:chemistry*; D008968:Molecular Conformation; D009025:Morpholines / Q000737:chemistry*; D010077:Oxazepines / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D001388:Aziridines; D004852:Epoxy Compounds; D009025:Morpholines; D010077:Oxazepines