title: Radical-mediated diamination of alkenes with phenylhydrazine and azodicarboxylates: highly diastereoselective synthesis of trans-diamines from cycloalkenes.
abstract: Metal-free synthesis: Diamination of alkenes by using phenylhydrazine and azodicarboxylates could be achieved in a one-pot manner under very mild conditions (see scheme; Boc = tert-butoxycarbonyl). This process works with the assistance of acetic acid by means of a radical mechanism and displays a high trans selectivity when cycloalkene substrates were used in the reaction.
authors.affiliation: Division of Chemistry and Biological Chemistry School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371.
authors.forename: Ming-Kui
authors.initials: MK
authors.lastname: Zhu
authors.forename: Yu-Chen
authors.initials: YC
authors.lastname: Chen
authors.forename: Teck-Peng
authors.initials: TP
authors.lastname: Loh
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D001391:Azo Compounds / Q000737:chemistry*; D003516:Cycloparaffins / Q000737:chemistry*; D003959:Diamines / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010659:Phenylhydrazines / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D001391:Azo Compounds; D003516:Cycloparaffins; D003959:Diamines; D010659:Phenylhydrazines