title: Transition metal-free generation of N-unsubstituted imines from benzyl azides: synthesis of N-unsubstituted homoallylic amines.
abstract: An efficient transition metal-free approach for the generation of N-unsubstituted imines from azides followed by trapping with allyl nucleophile to provide N-unsubstituted homoallylic amines has been described. Although catalytic KO(t)Bu in DMSO is sufficient to allow imine generation, stoichiometric KO(t)Bu is essential in THF. Further, an enantio- and diastereoselective synthesis of homoallylic amines from benzyl azide has also been exemplified.
authors.affiliation: Department of Chemistry, Indian Institute of Science Education and Research Bhopal, Indore By-pass Road, Bhauri, Bhopal 462066, India.
authors.forename: Suman
authors.initials: S
authors.lastname: Pramanik
authors.affiliation: Department of Chemistry, Indian Institute of Science Education and Research Bhopal, Indore By-pass Road, Bhauri, Bhopal 462066, India.
authors.forename: Reddy Rajasekhar
authors.initials: RR
authors.lastname: Reddy
authors.affiliation: Department of Chemistry, Indian Institute of Science Education and Research Bhopal, Indore By-pass Road, Bhauri, Bhopal 462066, India.
authors.forename: Prasanta
authors.initials: P
authors.lastname: Ghorai
mesh_terms: D000588:Amines / Q000138:chemical synthesis; D001386:Azides / Q000737:chemistry*; D001593:Benzyl Compounds / Q000737:chemistry*; D002384:Catalysis; D004121:Dimethyl Sulfoxide / Q000737:chemistry*; D007097:Imines / Q000138:chemical synthesis*; D015394:Molecular Structure; D013237:Stereoisomerism; D028561:Transition Elements / Q000737:chemistry*
chemical_list: D000588:Amines; D001386:Azides; D001593:Benzyl Compounds; D007097:Imines; D028561:Transition Elements; D004121:Dimethyl Sulfoxide