Synthesis of alfa-Hydrazino Ketones via Region- and Stereoselective Electrophilic Amination of Manganese Enolates and Enamines
Gabriela Dessole, Luca Bernardi, Bianca F. Bonini, Elena Capitò, Mariafrancesca Fochi, Raquel P. Herrera, Alfredo Ricci, Gérard Cahiez. Synthesis of alfa-Hydrazino Ketones via Region- and Stereoselective Electrophilic Amination of Manganese Enolates and Enamines. J. Org. Chem. . 2004, Vol. 69 / 2004, p. 8525-2004.
<p>A straightforward procedure for the regio- and stereoselective synthesis of R-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 a-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.</p>
<p>A straightforward procedure for the regio- and stereoselective synthesis of R-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 a-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.</p>