title: Synthesis of alpha-hydrazino ketones via regio- and stereoselective electrophilic amination of manganese enolates and enamines.
abstract: A straightforward procedure for the regio- and stereoselective synthesis of alpha-hydrazino ketones is described. Manganese enolates and manganese enamines derived from ketones and from the corresponding N-sulfinylimines react with azodicarboxylate esters (DTBAD and DEAD) in a regioselective fashion to afford in good to excellent yields the kinetic alpha-hydrazino ketones as sole or highly prevalent products. When enantiopure N-sulfinyl manganese enamines were used the stereoselectivity of these reactions ranged from 40% to 68% ee.
authors.affiliation: Dipartimento di Chimica Organica A. Mangini, Facoltà di Chimica Industriale, Università di Bologna, Viale Risorgimento 4, 40136 Bologna, Italy.
authors.forename: Gabriella
authors.initials: G
authors.lastname: Dessole
authors.forename: Luca
authors.initials: L
authors.lastname: Bernardi
authors.forename: Bianca F
authors.initials: BF
authors.lastname: Bonini
authors.forename: Elena
authors.initials: E
authors.lastname: Capito
authors.forename: Mariafrancesca
authors.initials: M
authors.lastname: Fochi
authors.forename: Raquel P
authors.initials: RP
authors.lastname: Herrera
authors.forename: Alfredo
authors.initials: A
authors.lastname: Ricci
authors.forename: Gérard
authors.initials: G
authors.lastname: Cahiez