Enantioselective syntheses of morpholines and their homologues via S(N)2-type ring opening of aziridines and azetidines with haloalcohols.
A highly regio- and stereoselective strategy for the syntheses in high yield and enantioselectivity of a variety of substituted nonracemic morpholines and their homologues is described. The reaction proceeds via an S(N)2-type ring opening of activated aziridines and azetidines by suitable halogenated alcohols in the presence of Lewis acid followed by base-mediated intramolecular ring closure of the resulting haloalkoxy amine.
Ghorai
Manas K
MK
Department of Chemistry, Indian Institute of Technology, Kanpur 208016, India. mkghorai@iitk.ac.in
Shukla
Dipti
D
Das
Kalpataru
K
D000438:Alcohols / Q000737:chemistry*; D000588:Amines / Q000737:chemistry; D001384:Azetidines / Q000737:chemistry*; D001388:Aziridines / Q000737:chemistry*; D006846:Hydrocarbons, Halogenated / Q000737:chemistry*; D009025:Morpholines / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000438:Alcohols; D000588:Amines; D001384:Azetidines; D001388:Aziridines; D006846:Hydrocarbons, Halogenated; D009025:Morpholines; C059688:alkoxyl radical