Synthesis of alpha-hydrazino ketones via regio- and stereoselective electrophilic amination of manganese enolates and enamines.
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.
Dessole
Gabriella
G
Dipartimento di Chimica Organica A. Mangini, Facoltà di Chimica Industriale, Università di Bologna, Viale Risorgimento 4, 40136 Bologna, Italy.
Bernardi
Luca
L
Bonini
Bianca F
BF
Capito
Elena
E
Fochi
Mariafrancesca
M
Herrera
Raquel P
RP
Ricci
Alfredo
A
Cahiez
Gérard
G