title: Stereoselective synthesis of activated 2-arylazetidines via imino-aldol reaction.
abstract: A simple and efficient synthetic route to substituted N-sulfinyl and N-sulfonyl azetidines is described involving imino-aldol reaction of ester enolates with racemic and non-racemic aldimines for obtaining β-amino esters as a key step. These β-amino esters on subsequent reduction followed by TsCl/KOH mediated cyclization produced the corresponding racemic and non-racemic azetidines with high yield and stereoselectivity.
authors.affiliation: Department of Chemistry, Indian Institute of Technology Kanpur, Kanpur 208016, India. mkghorai@iitk.ac.in.
authors.forename: Manas K
authors.initials: MK
authors.lastname: Ghorai
authors.forename: Subhomoy
authors.initials: S
authors.lastname: Das
authors.forename: Kalpataru
authors.initials: K
authors.lastname: Das
authors.forename: Amit
authors.initials: A
authors.lastname: Kumar
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D001384:Azetidines / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D004952:Esters / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D001384:Azetidines; D004952:Esters; D007097:Imines; C116609:3-hydroxybutanal